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- Herausgeber: John Wiley & Sons
- Kategorie: Wissenschaft und neue Technologien
- Sprache: Englisch
Integral, reliable, and comprehensive guidance for chemists performing the complex syntheses required for the formation and cleavage of protective groups
Organic synthesis is the preparation and creation of organic compounds for use in natural products, pharmaceuticals, and other molecules. The synthesis of molecules having multiple functional groups often requires the use of ‘protective groups’ to achieve site selectivity in a chemical reaction within a molecule bearing multiple sites of reactivity. Protective groups are installed temporarily to prevent unwanted reactions at a particular site, while transforming a different functional group. Once they have served their function, they are removed to expose the original group. Without a thorough understanding of the methods required to install and remove them, the design of a synthesis of a molecule having multiple functional groups in most cases is effectively impossible.
Greene’s Protective Groups in Organic Synthesis, 6th Edition is the definitive compilation of protective groups, their classification, and their application in a wide array of situations. With a long tradition of comprehensive coverage, organized on the basis of the functional group in need of protection and subsequent deprotection, it is an essential reference and resource for all chemists involved in organic syntheses. Now fully updated to reflect the current state of the art, it remains an indispensable resource for generating life-changing organic products. This edition contains a new chapter on how protective groups effect reactivity and selectivity in carbohydrate chemistry.
Readers of the sixth edition of Greene’s Protective Groups in Organic Synthesis will also find:
- Methodology for planning selectivity in organic syntheses
- Detailed discussion of all major functional groups including ethers, amides, and phenols
- A discussion of the impact of protective groups on reactivity in carbohydrates
Greene’s Protective Groups in Organic Synthesis is ideal for synthetic organic chemists or medicinal chemists in academia, industry — pharmaceuticals, food, agrochemicals, and biotech — or government agencies.
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Veröffentlichungsjahr: 2025
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Table of Contents
COVER
TABLE OF CONTENTS
VOLUME 1
TITLE PAGE
COPYRIGHT PAGE
DEDICATION
PREFACE
ABBREVIATIONS
PROTECTIVE GROUPS
ABBREVIATIONS REAGENTS
1 THE ROLE OF PROTECTIVE GROUPS IN ORGANIC SYNTHESIS
PROPERTIES OF A PROTECTIVE GROUP
HISTORICAL DEVELOPMENT
DEVELOPMENT OF NEW PROTECTIVE GROUPS
SELECTION OF A PROTECTIVE GROUP FROM THIS BOOK
SYNTHESIS OF COMPLEX SUBSTANCES. TWO EXAMPLES (AS USED IN THE SYNTHESIS OF HIMASTATIN AND PALYTOXIN) OF THE SELECTION, INTRODUCTION, AND REMOVAL OF PROTECTIVE GROUPS
2 PROTECTION FOR THE HYDROXYL GROUP INCLUDING 1,2- AND 1,3-DIOLS
ETHERS
ESTERS
PROTECTION FOR 1,2- AND 1,3-DIOLS
3 PROTECTION FOR PHENOLS AND CATECHOLS
PROTECTION FOR PHENOLS AND CATECHOLS
PROTECTION FOR CATECHOLS (1,2-DIHYDROXYBENZENES)
PROTECTION FOR 2-HYDROXYBENZENETHIOLS
4 PROTECTION FOR THE CARBONYL GROUP
ACETALS AND KETALS
MISCELLANEOUS DERIVATIVES
PROTECTION OF THE CARBONYL GROUP AS AN ENOLATE ANIONS, ENOL ETHERS, ENAMINES, AND IMINES
MONOPROTECTION OF DICARBONYL COMPOUNDS
5 PROTECTION FOR THE CARBOXYL GROUP
ESTERS
AMIDES AND HYDRAZIDES
PROTECTION OF SULFONIC ACIDS
PROTECTION OF BORONIC ACIDS
6 PROTECTION FOR THE THIOL GROUP
THIOETHERS
THIOESTERS
MISCELLANEOUS DERIVATIVES
VOLUME 2
TITLE PAGE
COPYRIGHT PAGE
DEDICATION
PREFACE
ABBREVIATIONS
PROTECTIVE GROUPS
ABBREVIATIONS REAGENTS
7 PROTECTION FOR THE AMINO GROUP
INTRODUCTION TO AMINES
CARBAMATES
AMIDES
SPECIAL –NH PROTECTIVE GROUPS
N
-HETEROATOM DERIVATIVES
PROTECTION OF AMINO ALCOHOLS
PROTECTION FOR IMIDAZOLES, PYRROLES, INDOLES, AND OTHER AROMATIC HETEROCYCLES
PROTECTION FOR THE AMIDE ─NH
PROTECTION FOR THE SULFONAMIDE ─NH
8 PROTECTION FOR THE ALKYNE ─CH
9 PROTECTION FOR THE PHOSPHATE GROUP
INTRODUCTION
SOME GENERAL METHODS FOR PHOSPHATE ESTER FORMATION
REMOVAL OF PROTECTIVE GROUPS FROM PHOSPHORUS
ALKYL PHOSPHATES
PHOSPHATES CLEAVED BY CYCLODEESTERIFICATION
2-SUBSTITUTED ETHYL PHOSPHATES
HALOETHYL PHOSPHATES
BENZYL PHOSPHATES
PHENYL PHOSPHATES
PHOTOCHEMICALLY CLEAVED PHOSPHATE PROTECTIVE GROUPS
AMIDATES
MISCELLANEOUS DERIVATIVES
10 PROTECTING GROUP EFFECTS IN CARBOHYDRATE CHEMISTRY
INTRODUCTION
AGLYCONE TRANSFER
PARTICIPATING GROUPS
CONFORMATIONAL RESTRICTION
SILYL GROUPS: CONFORMATIONAL AND REACTIVITY EFFECT
AMINO SUGAR PROTECTION
INTRODUCTION TO THE FORMATION OF SIALYL GLYCOSIDES
PROTECTING GROUP EFFECTS IN THE GLYCOSYLATION OF 2-DEOXY SUGARS
FURANOSIDES
PROTECTING GROUP EFFECTS ON ACCEPTORS
C
-GLYCOSYLATION
SPHINGOLIPIDS
11 REACTIVITIES, REAGENTS, AND REACTIVITY CHARTS
REACTIVITIES
REAGENTS
REACTIVITY CHARTS
INDEX
END USER LICENSE AGREEMENT
List of Tables
Chapter 2
Table 1 Removal Time in TFA/CH
2
Cl
2
(v/v)
Table 1 Relative Cleavage Rates for Selected Ethers of a Primary Alcohol
Table 2 Relative Cleavage Rates of Various Ethers of a Secondary Alcohol
Table 1 Relative Cleavage Rates for Various Uridine Protected Acetals
Table 1 Cleavage of Substituted Allyl Octyl Ethers Promoted by CeCl
3
·7H
2
O
Table 1 Approximate Half-Life of Various Allylic Ethers in Wet CD
2
Cl
2
at 80°C ...
Table 1 Relative Rates for Substituted Benzyl Ether Cleavage
Table 2 Solvent Effect on the Hydrogenation of Benzyl Ether at 1.1 bar H
2
at 5...
Table 1 Cleavage of MPM, DMPM, and TMPM Ethers with DDQ in CH
2
Cl
2
/H
2
O at 20°C...
Table 1 Relative Reactivity of PSB, Bn, and TBS Ethers
Table 1 Relative Rates of Silyl Ether Cleavage
Table 1 Half-Lives for Hydrolysis of Various Esters
Table 1 Cleavage Rates for 4-Substituted Psec Derivatives
Table 1 Acidic Hydrolysis of 2′,3′-Protected Uridine Derivatives
Chapter 4
Table 1 Relative Hydrolysis Rates of α-Androstane Cyclic Ketals in 0.02
N
HCl ...
Table 1 Olefin Isomerization as a Function of Acid p
K
a
.
Chapter 7
Table 1Time for Complete Deblocking of Substituted Urethanes by Various Amine ...
Table 1 Relative Efficiency of Allyl Group Scavengers with Pd(Ph3P)4 as Cataly ...
Table 1Comparison Between Fmoc and Nsc Protected Peptides
Chapter 10
Table 1Reactivity Based on Leaving Group with I
2
Promoter
Table 2Relative Reactivity of Armed and Superarmed Donors with Different Prom ...
Table 1Effect of Donor-Protecting Group Arrangement on Schmidt Glycosylation ...
Table 2Glycosylation with the ADMB Group at the 2-Position
Table 1Is C4 Participation in Mannose Relevant
Table 2Effect of C4 Esters as SBox Donors
Table 1Effect of 2,3,4-
O
-Substituents on Selectivity
Table 2β-Rhamnosylation with Orthocarbonate Donor from Entry 5 in Table 1 ...
Table 1−ΔG° Values for the Ring Inversion of Cyclohexyl Silyl Ethers ...
Table 2ΔG° Values for Ring Inversion of cis-4-Methylcyclohexyl Silyl Ethers ...
Table 3% Axial Conformer as a Function of Silyl Group in 1,4-Substituted Cycl ...
Table 4% Axial Conformer as a Function of Silyl Group in 1,2-Substituted Cycl ...
Table 1DMTST Activation of Different Amine-Protected Sialyl Donors
Table 2NIS/TfOH Activation of Different Amine-Protected Sialyl Donors
Table 1Effect of Donor-Leaving Group and Acceptor-Protecting Group
Table 2Benzoate Versus Benzyl Effect on O2, O3, and O4 Glycosylations
List of Illustrations
Chapter 1
Scheme 1 Preparation of the pyrroloindoline
Scheme 2 Preparation of pyrroloindoline dimer
Scheme 3 Protecting group manipulations on dimer
Scheme 4 Preparation of the piperazyl piece
Scheme 5 Peptide formation
Scheme 6 Coupling of the units and deprotection
Figure 1 Palytoxin carboxylic acid.
Chapter 9
Scheme 1 Automated synthesis of oligonucleotides. Synthetic cycle for the phos...
Chapter 10
Scheme 1 Initial attempt at Synthesis of Herbicidin
Scheme 2 Synthesis of Herbicidin based on silyl induced conformational flip.
Guide
Cover Page
Title Page
Copyright Page
Dedication
Preface
Abbreviations
Title Page
Copyright Page
Dedication
Preface
Abbreviations
Table of Contents
Begin Reading
Index
WILEY END USER LICENSE AGREEMENT
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GREENE’S PROTECTIVE GROUPS IN ORGANIC SYNTHESIS
Sixth Edition
VOLUME 1
PETER G. M. WUTS
Kalamazoo, Michigan, USA
Copyright © 2025 by John Wiley & Sons, Inc. All rights reserved, including rights for text and data mining and training of artificial intelligence technologies or similar technologies.
Published by John Wiley & Sons, Inc., Hoboken, New Jersey.Published simultaneously in Canada.
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Library of Congress Cataloging-in-Publication Data applied for
Hardback ISBN: 9781394233168 [Set]Hardback ISBN: 9781394319343 [Volume 1]Hardback ISBN: 9781394319350 [Volume 2]ePDF ISBN: 9781394233175ePUB ISBN: 9781394233182oBook ISBN: 9781394233199
Cover Design: WileyCover Images: © Elizabeth Contessa Wuts
DEDICATION
This volume is dedicated to the memory of my loyal assistant Osiris Wuts.
PREFACE
This edition has maintained the tradition of the previous five editions. The literature cutoff was the end of February 2024, which covers nearly 10 years since the last edition. I have processed over 4000 references of which a little over 3000 of these have been put in the new addition. I have been as all-inclusive as possible since this book is meant to provide as many options as possible for protection and deprotection.
Although there are numerous papers with titles like “Protecting group free synthesis of X,” we have a long way to go before protecting groups will not be used in chemical synthesis.
This edition includes a new chapter on how protecting groups affect the glycosylation process, a subject that has interested me since I started working on the second edition. I have limited the chapter to carbohydrates due to the sheer volume of literature that would need to be covered. This new chapter is divided into sections that cover different situations where protecting groups influence reactivity and stereoselectivity. When going through the chapter the reader will find that there is some overlap between sections since the publications cited, often present information in multiple areas. I have included a number of tables illustrating how various protecting group arrangements influence reaction outcomes. Being an organic chemist looking at structures and drawing conclusions is much more instructive than trying to do this in print. I have tried to organize related systems together as much as possible to simplify the examination of a particular concept. For example, how do various conformational restraints influence the outcome of a glycosylation.
In conclusion, I thank Jonathan Rose my editor for giving me this opportunity during my so-called retirement. Again, I thank Jed Fisher, who gave me a copy of his extensive database which included many useful references. I must also thank Western Michigan University for giving me an Adjunct Professorship, allowing me access to their library which has helped me keep up with the literature. My greatest thanks must go to my wife, Lizzie, who has encouraged me to do this edition and who printed out over 3000 references since it is difficult to read papers on the computer. As always, she brings me a glass of wine at the end of my evening session of working on the book.
Peter G. M. Wuts
February 2025
ABBREVIATIONS
PROTECTIVE GROUPS
In some cases, several abbreviations are used for the same protective group. We have listed the abbreviations as used by an author in his original paper, including capital and lower-case letters. Occasionally, the same abbreviation has been used for two different protective groups. This information is also included.
ABO
2,7,8-trioxabicyclo[3.2.1]octyl
Ac
acetyl
ACBZ
4-azidobenzyloxycarbonyl
ACE
O
-bis(2-Acetoxyethoxy)methyl
AcHmb
2-acetoxy-4-methoxybenzyl
Acm
acetamidomethyl
a-CNV-OPh
α-carboxy-6-nitroveratryl
Ad
1-adamantyl
ADMB
4-acetoxy-2,2-dimethylbutanoate
Adoc
1-adamantyloxycarbonyl
Adpoc
1-(1-adamantyl)-1-methylethoxycarbonylAIBNAzobisisobutyronitrile
Alloc or AOC
allyloxycarbonyl
AOC or Alloc
allyloxycarbonyl
Allocam
allyloxycarbonylaminomethyl
Als
allylsulfonyl
AMB
2-(acetoxymethyl)benzoyl
AMPA
(2-azidomethyl)phenylacetate
AN
4-methoxyphenyl or anisyl
Ans
anisylsulfonyl
Anpe
2-(4-acetyl-2-nitrophenyl)ethyl
p
-AOM
p
-anisyloxymethyl or (4-methoxyphenoxy)methyl
APAC
2-allyloxyphenylacetate
Aqmoc
anthraquinone-2-ylmethoxycarbonyl
Azb
p
-azidobenzyl
Azm
azidomethyl
AZMB
2-(azidomethyl)benzoate
Bam
benzamidomethyl
BBA
butane-2,3-bisacetal
Bbc
but-2-ynylbisoxycaronyl
BDIPS
biphenyldiisopropylsilyl
benzoyldiisopropylsilyl
BDMS
biphenyldimethylsilyl
benzyldimethylsilyl
Bdt
1,3-benzodithiolan-2-yl
Betsyl or Bts
benzothiazole-2-sulfonyl
Bhcmoc
6-bromo-7-hydroxycoumarin-4-ylmethoxycarbonyl
BHQ
8-bromo-7-hydroxyquinoline-2-ylmethyl
BHT
2,6-di-
t
-butyl-4-methylphenyl
BIBS
di-
t
-butylisobutylsilyl
Bic
5-benzisoxazolylmethoxycarbonyl
Bim
5-benzisoazolylmethylene
Bimoc
benz[
f
]inden-3-ylmethoxycarbonyl
BIPSOP
N
-2,5-bis(triisopropylsiloxy)pyrrolyl
Bloc
1-buten-4-yl
BMB
o
-(benzoyloxymethyl)benzoyl
Bmpc
2,4-dimethylthiophenoxycarbonyl
Bmpm
bis(4-methoxyphenyl)-1′-pyrenylmethyl
Bn
benzyl
Bnf
fluorousbenzyl
Bno
tri-
n
-butylmethyl
Bnpeoc
2,2-bis(4′-nitrophenyl)ethoxycarbonyl
Bns
benzylsulfonate
BOB
Benzyloxybutyrate
BOC
t
-butoxycarbonyl
Bocdene
2-(
t
-butylcarbonyl)ethylidene
BOM
benzyloxymethyl, beer of the month
bpa
bispicolylamide
Bpoc
1-methyl-1-(4-biphenyl)ethoxycarbonyl
BSB
benzostabase
Bsmoc
1,1-dioxobenzo[
b
]thiophene-2-ylmethoxycarbonyl
BTM
t
-butylthiomethyl
Bts or Betsyl
benzothiazole-2-sulfonyl
B
t
SE
2-
t
-butylsulfonylethyl
Bts-Fmoc
2,7-bis(trimethylsilyl)fluorenylmethoxycarbonyl
Bum
t-
butoxymethyl
Bus
t
-butylsulfonyl
t-
Bumeoc
1-(3,5-di-
t
-butylphenyl)-1-methylethoxycarbonyl
Bz
benzoyl
Bz-NPPOC
2-(5-benzoyl-2-nitrophenyl)propyl
CAEB
2-[(2-chloroacetoxy)ethyl]benzoyl
Cam
carboxamidomethyl
CAMB
2-(chloroacetoxymethyl)benzoyl
Cbz or Z
benzyloxycarbonyl
CEM
2-cyanoethoxymethyl
CDA
cyclohexane-1,2-diacetal
CDM
2-cyano-1,1-dimethylethyl
CE or Cne
2-cyanoethyl
Cee
1-(2-chloroethoxy)ethyl
CEE
1-(2-cyanoethoxy)ethyl
Ceof
cyclic ethyl orthoformate
cHex
cyclohexyl
cHBS
di-
tert
-butyl(cyclohexyl)silyl
Chx
cyclohexyl
Cin
cinnamyl
ClAzab
4-azido-3-chlorobenzyl
Climoc
2-chloro-3-indenylmethoxycarbonyl
Cms
carboxymethylsulfenyl
CNAP
2-naphthylmethoxycarbonyl
Cne or CE
2-cyanoethyl
Coc
cinnamyloxycarbonyl
CPC
p
-chlorophenylcarbonyl
CPDMS
(3-cyanopropyl)dimethylsilyl
Cpeoc
2-(cyano-1-phenyl)ethoxycarbonyl
Cpep
1-(4-chlorophenyl)-4-methoxypiperidin-4-yl
CPTr
4,4′,4″-tris(4,5-dichlorophthalimido)triphenylmethyl
CTFB
4-trifluoromethylbenzyloxycarbonyl
CTMP
1-[(2-chloro-4-methyl)phenyl]-4-methoxypiperidin-4-yl
Cyclo-SEM
5-trimethylsilyl-1,3-dioxane
Cys
cysteine
DAM
di-
p
-anisylmethyl or bis(4-methoxyphenyl)methyl
2′-
O
-{[2,2-dimethyl-2-(2-nitrophenyl)acetyl]oxy}methyl
DATE
1,1-di-
p
-anisyl-2,2,2-trichloroethyl
DB-
t
-BOC
1,1-dimethyl-2,2-dibromoethoxycarbonyl
DBD-Tmoc–NR2
2,7-Di-
t
-butyl[9-(10,10-dioxo-10,10,10,10-tetrahydrothioxanthyl)]methyl Carbamate
DBS
dibenzosuberyl
DCP
dichlorophthalimide
Dcpm
dicyclopropylmethyl
Ddm or Dmbh
bis(4-methoxyphenyl)methyl
Dde
2-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl
Ddz
1-methyl-1-(3,5-dimethoxyphenyl)ethoxycarbonyl
DEABn
3-diethylaminobenzyl
DEAPE
1-(3-(diethylamino)phenyl)ethyl
DEM
diethoxymethyl
DEIPS
diethylisopropylsilyl
Desyl
2-oxo-1,2-diphenylethyl
Dim
1,3-dithianyl-2-methyl
DIMON
1,4-dimethoxynaphthalene-2-methylDMAdimethylacetamide
Dmab
4-{
N
-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino}benzyl
Dmaoc
N,N
-dimethylamonoxy
DMATr
(3-(dimethylamino)phenyl)diphenylmethyl
DMB
3′,5′-dimethoxybenzoin
Dmb
2,4-dimethoxybenzyl
DMBM
[(3,4-dimethoxybenzyl)oxy]methyl
dMDmoc
2-(1,3-dithian-2-yl)propan-2-yl
Dmepa
dimethylaminoethylpicolylamide
DMIPS
dimethylisopropylsilyl
DMN
2,3-dimethylmaleimide
Dmoc
dithianylmethoxycarbonyl
Dmp
2,4-dimethyl-3-pentyl
Dmp
dimethylphosphinyl
DMP
dimethoxyphenyl
dimethylphenacyl
DMPM
3,4-dimethoxybenzyl
DMTC
dimethylthiocarbamate
DMT or DMTr
di(
p
-methoxyphenyl)phenylmethyl or dimethoxytrityl
DMTr or DMT
di(
p
-methoxyphenyl)phenylmethyl or dimethoxytrityl
DNAP
2-(dimethylamino)-5-nitrophenyl
DNB
p
,
p
′-dinitrobenzhydryl
DNMBS
4-(4′,8′-dimethoxynaphthylmethyl)benzenesulfonyl
DNP
2,4-dinitrophenyl
Dnpe
2-(2,4-dinitrophenyl)ethyl
Dnpeoc
2-(2,4-dinitrophenyl)ethoxycarbonyl
DNs
2,4-dinitrobenzenesulfonyl
DNse
2-(2,4-dinitrophenylsulfonyl)ethoxycarbonyl
Dnseoc
2-dansylethoxycarbonyl
Dobz
p
-(dihydroxyboryl)benzyloxycarbonyl
Doc
2,4-dimethylpent-3-yloxycarbonyl
Dod
bis(4-methoxylphenyl)methyl
DOPS
dimethyl[1,1-dimethyl-3-(tetrahydro-2
H-
pyran-2-yloxy)propyl]silyl
DPA
diphenylacetyl
Dpaa
2-(di(pyridin-2-yl)amino)acetamide
DPIPS
diphenylisopropylsilyl
DPM or Dpm
diphenylmethyl
DPMS
diphenylmethylsilyl
Dpp
diphenylphosphinyl
Dppe
2-(diphenylphosphino)ethyl
Dppm
(diphenyl-4-pyridyl)methyl
DPSE
2-(methyldiphenylsilyl)ethyl
DPSide
diphenylsilyldiethylene
Dpt
diphenylphosphinothioyl
DPTBOS
t
-butoxydiphenylsilyl
DPTBS
diphenyl-
t
-butoxysilyl or
diphenyl-
t
-butylsilyl
Dtb-Fmoc
2,6-di-
t
-butyl-9-fluorenylmethoxycarbonyl
DTBMS
di-
t-
butylmethylsilyl
DTBS
di-
t
-butylsilylene
DTE
2-(hydroxyethyl)dithioethyl or “dithiodiethanol”
Dts
dithiasuccinimidyl
E-DMT
1,2-ethylene-3,3-bis(4′4″-dimethoxytrityl)EDTethane-1,2-dithiol
EE
1-ethoxyethyl
EOM
ethoxymethyl
Epin
1,1,2,2-Tetraethylethylene glycol
F
Cbz
fluorous benzyloxycarbonyl
Fcm
ferrocenylmethyl
Flu
fluorenyl
Fm
9-fluorenylmethyl
Fmoc
9-fluorenylmethoxycarbonyl
Fpmp
1-(2-fluorophenyl)-4-methoxypiperidiny-4-yl
Fsec
2-[4-fluorophenyl)-sulfonyl]ethyl
GUM
guaiacolmethyl
HAPE
1-[2-(2-hydroxyalkyl)phenyl]ethanone
HBn
2-hydroxybenzyl
Hdoc
hexadienyloxycarbonyl
HFB
hexafluoro-2-butyl
HFIA
dimethyl 2-(alkoxyoxymethoxy)isophthalate
HIP
1,1,1,3,3,3-hexafluoro-2-phenylisopropyl
Hoc
cyclohexyloxycarbonyl
HSDIS
(hydroxystyryl)diisopropylsilyl
HSDMS
(hydroxystyryl)dimethylsilyl
hZ or homo Z
homobenzyloxycarbonyl
ICPrc
3-isocyanopropyl
IDTr
3-(imidazol-1-ylmethyl)-4′,4″-dimethoxytriphenylmethyl
IETr
4,4′-dimethoxy-3″-[
N
-(imidazolylethyl)carbamoyl]trityl
iMds
2,6-dimethoxy-4-methylbenzenesulfonyl
Ipaoc
1-isopropylallyloxycarbonyl
Ipc
isopinocampheyl
IPDMS
isopropyldimethylsilylLEDLight emitting diode
Lev
levulinoyl
LevS
4,4-(ethylenedithio)pentanoyl
LevS
levulinoyldithioacetal ester
LMM
o
(
p
)NBz
6-(levulinyloxymethyl)-3-methoxy-2-nitrobenzoate
MAB
2-{{[(4-methoxytrityl)thio]methylamino}methyl}benzoate
MAQ
2-(9,10-anthraquinonyl)methyl or 2-methyleneanthraquinone
MBE
1-methyl-1-benzyloxyethyl
Mbh
bis(4-methylphenyl)methyl
mBhc
6-bromo-7-hydroxy-3-methyl-4-((alkylthio)methyl)-2
H
-chromen-2-one
MBF
2,3,3a,4,5,6,7,7a-octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl
MBS or Mbs
p
-methoxybenzenesulfonyl
MCPM
1-Methyl-1′-cyclopropylmethyl
Mds
2,6-dimethyl-4-methoxybenzenesulfonyl
MDPS
methylene-bis-(diisopropylsilanoxanylidene
Me
methyl
ME
methoxyethyl
MEC
α-methylcinnamyl
Mee
methoxyethoxyethyl
MeOAc
methoxyacetate
MeO-CyHO
4-methoxy-(8-cyano-7-hydroxyquinolin-2-yl)methyl
MEM
2-methoxyethoxymethyl
Menpoc
α-methylnitropiperonyloxycarbonyl
MeO-NDBF
7-methoxy-2-(1-(alkylthio)ethyl)-3-nitrodibenzo[
b,d
]furan
MeOZ or Moz
p
-methoxybenzyloxycarbonyl
Mes
mesityl or 2,4,6-trimethylphenyl
MIP
methoxyisopropyl or 1-methyl-1-methoxyethyl
MM
menthoxymethyl
MMT or MMTr
p
-methoxyphenyldiphenylmethyl
MMTr or MMT
p
-methoxyphenyldiphenylmethyl
MMPPOC
2-(3,4-methylenedioxy-6-nitrophenypropyloxycarbonyl
Mmsb
3-methoxy-4-methylsufinylbenzyl
MNPPOC
2-(3,4-methylenedioxy-6-nitrophenylpropyl
MOB
2-{[(4-methoxytritylthio)oxy]methyl}benzoate
Mocdene
2-(methoxycarbonyl)ethylidene
MoEt
2-
N
-(Morpholino)ethyl
MOM
methoxymethyl
MOMO
methoxymethoxy
Moz or MeOZ
p
-methoxybenzyloxycarbonyl
MP
p
-methoxyphenyl
Mpe
3-methyl-3-pentyl
MPM or PMB
p
-methoxyphenylmethyl or
p
-methoxybenzyl
Mps
p-
methoxyphenylsulfonyl
Mpt
dimethylphosphinothioyl
Ms
methanesulfonyl or mesyl
MSE
2-(methylsulfonyl)ethyl
Msib
4-(methylsulfinyl)benzyl
Mspoc
2-methylsulfonyl-3-phenyl-1-prop-2-enyloxy
Msz
4-methylsulfinylbenzyloxycarbonyl
MTAD
4-methyl-1,2,4-triazoline-3,5-dione
Mtb
2,4,6-trimethoxybenzenesulfonyl
Mte
2,3,5,6-tetramethyl-4-methoxybenzenesulfonyl
MTHP
4-methoxytetrahydropyranyl
MTM
methylthiomethyl
MTMB
4-(methylthiomethoxy)butyryl
MTMECO
2-(methylthiomethoxy)ethoxycarbonyl
MTMT
2-(methylthiomethoxymethyl)benzoyl
Mtpc
4-(methylthio)phenoxycarbonyl
Mtr
2,3,6-trimethyl-4-methoxybenzenesulfonyl
Mts
2,4,6-trimethylbenzenesulfonyl or Mesitylenesulfonyl
Mtt
4-methoxytrityl
4-methyltrityl
Nap
2-napthylmethyl
NAPOM
2-naphthylmethoxymethyl
NBOM
nitrobenzyloxymethyl
NBM
nitrobenzyloxymethyl
NDBF
2-(1-(alkylthio)ethyl)-3-nitrodibenzo[
b,d
]furan
NDMS
2-norbornyldiemethylsilyl
Ne
2-nitroethyl
NNM
3-nitro-2-naphthylmethyl
Noc
4-nitrocinnamyloxycarbonyl
Nosyl or Ns
2- or 4-nitrobenzenesulfonyl
Npb
3-(2-nitrophenyl)butan-2-ol
Npe or npe
2-(nitrophenyl)ethyl
Npeoc
2-(4-nitrophenyl)ethoxycarbonyl
Npeom
[1-(2-nitrophenyl)ethoxy]methyl
Npes
2-(4-nitrophenyl)ethylsulfonyl
Nph
6-hydroxy-5-(2-nitrophenyl)heptanoic
Npp
2-(2-nitrophenyl)propyl
NPPOC
2-(2-nitrophenyl)propyloxycarbonyl
NPS or Nps
2-nitrophenylsulfenyl
NpSSPeoc
2-[(2-nitrophenyl)dithio]-1-phenylethoxycarbonyl
Npys
3-nitro-2-pyridinesulfenyl
Ns or Nosyl
2- or 4-nitrobenzenesulfonyl
Nse
2-(4-nitrophenylsulfonyl)ethoxycarbonyl
NVOC or Nvoc
3,4-dimethoxy-6-nitrobenzyloxycarbonyl or 6-nitroveratryloxycarbonyl
OBO
2,6,7-trioxabicyclo[2.2.2]octyl
O-DMT
3,3′-oxybis(dimethoxytrityl)
ONB
o
-nitrobenzyl
oNv
(4,5-dimethoxy-2-nitrophenyl)methylthio
PAB
p
-acylaminobenzyl
PAB
acetoxybenzyl
PAC
H
2-[2-(benzyloxy)ethyl]benzoyl
PAC
M
2-[2-(4-
methoxybenzyloxy)ethyl]benzoyl
Paloc
3-(3-pyridyl)allyloxycarbonyl or
3-(3-pyridyl)prop-2-enyloxycarbonyl
Pbf
2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl
PDNO
2,6-pyridinedicarboxylic acid
N
-oxide
PeNB
pentadienylnitrobenzyl
PeNP
pentadienylnitropiperonyl
Peoc
2-phosphonioethoxycarbonyl
Peoc
2-(triphenylphosphonio)ethoxycarbonyl
Pet
2-(2′-pyridyl)ethyl
Pf
9-phenylfluorenyl
Pfp
pentafluoropenyl
Phamc
phenylacetamidomethyl
PhAc
4-phenylacetoxybenzyloxycarbonyl
Phedec
phenyldithioethyl
Phenoc
4-methoxyphenacyloxycarbonyl
PhS-NPPOC
2-(4-ethyl-2-nitro-5-(phenylthio)phenyl)propyl
Pic
picolinate
Pim
phthalimidomethyl
PIP
2-(piperidine-1-yl)-ethyl
Piv
pivaloyl
Pixyl or Px
9-(9-phenyl)xanthenyl
PMB or MPM
p
-methoxybenzyl or
p
-methoxyphenylmethyl
PMBM
p
-methoxybenzyloxymethyl
Pmc
2,2,5,7,8-pentamethylchroman-6-sulfonyl
pMCB
4-(alkoxymethyl)benzoate
Pme
pentamethylbenzenesulfonyl
PMNB
2-(4′-methoxy-4-nitro-[1,1′-biphenyl]-3-yl)propan-1-ol
PMP
p
-methoxyphenyl
PMS
p
-methylbenzylsulfonyl
Pms
2-[phenyl(methyl)sulfonio]ethoxycarbonyl
PNB
p
-nitrobenzyl
p
-nitrobenzoate
p
NBZ
p
-nitrobenzoate
PNP
p
-nitrophenyl
PNPE
2-(4-nitrophenyl)ethyl
PNZ
p
-nitrobenzylcarbonyl
POC
propargyloxycarbonyl
POM
4-pentenyloxymethyl
POM
pivaloyloxymethyl
POM
[(
p
-phenylphenyl)oxy]methyl
POMB
2-(prenyloxy)methylbenzoate
Ppoc
2-triphenylphosphonioisopropoxycarbonyl
Pp
2-phenyl-2-propyl
Ppt
diphenylthiophosphinyl
Pre
prenyl
Preoc
prenyloxycarbonyl
Proc or Poc
propargyloxycarbonyl
PSB
p
-siletanylbenzyl
PSE
2-(phenylsulfonyl)ethyl
Psoc
(2-phenyl-2-trimethylsilyl)ethoxycarbonyl
Psec
2-(phenylsulfonyl)ethoxycarbonyl
PTE
2-(4-nitrophenyl)thioethyl
PTM
phenylthiomethyl
PTMSE
(2-phenyl-2-trimethylsilyl)ethyl
Pv
pivaloyl
Px or pixyl
9-(9-phenyl)xanthenyl
Pydec
2-pyridyldithioethyl
Pyet
1-(α-pyridyl)ethyl
Pyoc
2-(2′- or 4′-pyridyl)ethoxycarbonyl
Qn
2-quinolinylmethyl
Qm
2-quinolinylmethyl
QUI
4-quinolinylmethyl
SATE
S
-acetylthioethyl
Scm
S
-carboxymethylsulfenyl
SEE
1-[2-(trimethylsilyl)ethoxy]ethyl
SEM
2-(trimethylsilyl)ethoxymethyl
SES
2-(trimethylsilyl)ethanesulfonyl
SIBA
1,1,4,4-tetraphenyl-1,4-disilanylidene
Sisyl
tris(trimethylsilyl)silyl
SMOM
(phenyldimethylsilyl)methoxymethyl
Snm
S
-(
N
′-methyl-
N
′-phenylcarbamoyl)sulfenyl
SOB
4-trialkylsilyloxybutyrate
STABASE
1,1,4,4-tetramethyldisilylazacyclopentane
TAB
2-{[(methyl(tritylthio)amino]methyl}benzoate
Tacm
trimethylacetamidomethyl
TBDMS or TBS
t
-butyldimethylsilyl
TBDPS
t-
butyldiphenylsilyl
Tbf-DMTr
4-(17-tetrabenzo[
a
,
c
,
g
,
i
]fluorenylmethyl-4′,4″-dimethoxytrityl
Tbfmoc
17-tetrabenzo[
a
,
c
,
g
,
i
]fluorenylmethoxycarbonyl
TBDPSE
t
-butyldiphenylsilylethyl
TBDS
tetra-
t-
butoxydisiloxane-1,3-diylidene
Tbe
2-(
tert
-Butyldisulfaneyl)ethyl
TBMPS
t
-butylmethoxyphenylsilyl
TBS or TBDMS
t
-butyldimethylsilyl
TBTr
4,4′,4″-tris(benzyloxy)triphenylmethyl
TCB
2,2,2-trichloro-1,1-dimethylethyl
TcBOC
1,1-dimethyl-2,2,2-trichloroethoxycarbonyl
TCP
N
-tetrachlorophthalimido
Tcroc
2-(trifluoromethyl)-6-chromonylmethyleneoxycarbonyl
Tcrom
2-(trifluoromethyl)-6-chromonylmethylene
TDE
(2,2,2-trifluoro-1,1-diphenyl)ethyl
TDG
thiodiglycoloyl
TDS
thexyldimethylsilyl
tris(2,6-diphenylbenzyl)silyl
Tempoc
2,2,6,6-tetramethylpiperidin-1-yloxy
Teoc
2-(trimethylsilyl)ethoxycarbonyl
TES
triethylsilyl
Tf
trifluoromethanesulfonyl
TFA
trifluoroacetyl
Tfacm
S
-trifluoroacetamidomethyl
Tfav
4,4,4-trifluoro-3-oxo-1-butenyl
Tfe-Pocam
S-N
-trifluoromethylphenyacyloxycarbamidomethyl
Thexyl
2,3-dimethyl-2-butyl
THF
tetrahydrofuranyl
THP
tetrahydropyranyl
TIBS
triisobutylsilyl
TIPDS
1,3-(1,1,3,3-tetraisopropyldisiloxanylidene)
TIPS
TriisopropylsilylTIPSHtriisopropylsilane
TIX
trimethylsilylxylyl
TLTr
4,4′,4″-tris(levulinoyloxy)triphenylmethyl
Tmb
2,4,6-trimethylbenzyl
Tmob
trimethoxybenzyl
TMPM
trimethoxyphenylmethyl
TMS
trimethylsilyl
Tms
(2-methyl-2-trimethylsilyl)ethyl
TMSE or TSE
2-(trimethylsilyl)ethyl
TMSEC
2-(trimethylsilyl)ethoxycarbonylTMSItrimethylsilyliodide
TMSP
2-trimethylsilylprop-2-enyl
TMTr
tris(
p
-methoxyphenyl)methyl
TOB
2-{[(tritylthio)oxy]methyl}benzoate
Tos or Ts
p
-toluenesulfonyl
Tom
triisopropylsilyloxymethyl
TPS
triphenylsilyl
TPTE
2-(4-triphenylmethylthio)ethyl
Tr
triphenylmethyl or trityl
TrtF
7
2,3,4,4′,4″,5,6-heptafluorotriphenylmethyl
Tritylone
9-(9-phenyl-10-oxo)anthryl
Troc
2,2,2-trichloroethoxycarbonyl
Ts or Tos
p
-toluenesulfonyl
Tsc
2-(4-trifluoromethylphenylsulfonyl)ethoxycarbonyl
TSE or TMSE
2-(trimethylsilyl)ethyl
Tse
2-(
p-
toluenesulfonyl)ethyl
Tsoc
triisopropylsiloxycarbonyl
Tsv
p
-toluenesulfonylvinyl
VeZ
3-methoxy-4-(vinyloxy)benzyl
Voc
vinyloxycarbonyl
Xan
xanthenyl
Z or Cbz
benzyloxycarbonyl
ABBREVIATIONS REAGENTS
9-BBN
9-borabicyclo[3.3.1]nonane
bipy
2,2′-bipyridine
BOP reagent
benzotriazol-1-yloxytris(dimethylamino)phosphonium
hexafluorophosphate
BOP-Cl
Bis(2-oxo-3-oxazolidinyl)phosphinic chloride
BroP
bromotris(dimethylamino)phosphonium
hexafluorophosphate
Bt
benzotriazol-1-yl or 1-benzotriazolyl
BTEAC
benzyltriethylammonium chloride
CAL
Candida antarctica lipase
CAN
ceric ammonium nitrate
CMPI
2-chloro-1-methylpyridinium iodide
cod
cyclooctadiene
cot
cyclooctatetraene
CSA
camphorsulfonic acid
DABCO
1,4-diazabicyclo[2.2.2]octane
DBN
1,5-diazabicyclo[4.3.0]non-5-ene
DBAD
di
-t
-butyl azodicarboxylate
DBU
1,8-diazabicyclo[5.4.0]undec-7-ene
DCC
dicyclohexylcarbodiimide
DDQ
2,3-dichloro-5,6-dicyano-1,4-benzoquinone
DEAD
diethyl azodicarboxylate
DIAD
diisopropyl azodicarboxylate
DIBAL-H
diisobutylaluminum hydride
DIPEA
diisopropylethylamine
DMAC
N,N
-dimethylacetamide
DMAP
4-
N,N
-dimethylaminopyridine
DMB
2,4-dimethoxybenzyl
DMDO
2,2-dimethyldioxirane
DME
1,2-dimethoxyethane
DMF
N,N
-dimethylformamide
DMPU
1,3-dimethyl-3,4,5,6-tetrahydro-2(1
H
)-pyrimidinone
DMS
dimethyl sulfide
DMSO
dimethyl sulfoxide
dppb
1,4-bis(diphenylphosphino)butane
dppe
1,2-bis(diphenylphosphino)ethane
DTE
dithioerythritol
DTT
dithiothreitol
EDC or EDCI
1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (or
1-[3-(dimethylamino)propyl]-3-ethylcarbodimide) hydrochloride
EDCI or EDC
1-ethyl-3-(3-(dimethylaminopropyl)carbodiimide
EDTA
ethylenediaminetetraacetic acid
HATU
N
-[(dimethylamino)(3
H
-1,2,3-triazolo(4,5-
b
)pyridin-3-yloxy)methylene]-
N-
methylmethanaminium hexafluorophosphate, previously known as
O
-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate.
HFIP
hexafluorisopropyl
HMDS
1,1,1,3,3,3-hexamethyldisilazane
HMPA
hexamethylphosphoramide
HMPT
hexamethylphosphorous triamide
HOAt
7-aza-1-hydroxybenzotriazole
HOBT
1-hydroxybenzotriazole
Im
imidazol-1-yl or 1-imidazolyl
IPA
isopropyl alcohol
IPCF (=IPCC)
isopropenyl chloroformate (isopropenyl chlorocarbonate)
KHMDS
potassium hexamethyldisilazide
LAH
lithium aluminum hydride
LDBB
lithium 4,4′-di-
t
-butylbiphenylide
MAD
methylaluminumbis(2,6-di-
t
-butyl-4-methylphenoxide
MCPBA
m
-chloroperoxybenzoic acid
MoOPH
oxodiperoxymolybdenum(pyridine)hexamethylphosphoramide
MS
molecular sieves
MSA
methanesulfonic acid
MTB
methylthiobenzene
MTBE
t
-butyl methyl ether
NBS
N
-bromosuccinimide
Ni(acac)
2
nickel acetylacetonate
NMM
N
-methylmorpholine
NMO
N
-methylmorpholine
N
-oxide
NMP
N
-methylpyrrolidinone
P
polymer support
Pc
phthalocyanine
PCC
pyridinium chlorochromate
PdCl
2
(tpp)
2
dichlorobis[tris(2-methylphenyl)phosphine]palladium
Pd
2
(dba)
3
tris(dibenzylideneacetone)dipalladium
PG
protective group
PhI(OH)OTs
[hydroxy(tosyloxy)iodo]benzene
PPL
porcine pancreatic lipase
PPTS
pyridinium
p
-toluenesulfonate
proton sponge
1,8-bis(dimethylamino)naphthalene
Pyr
pyridine
Rh
2
(pfb)
4
rhodium perfluorobutyrate
ScmCl
methoxycarbonylsulfenyl chloride
SMEAH
sodium bis(2-methoxyethoxy)aluminum hydride
Su
succinimidyl
TAS-F
tris(dimethylamino)sulfonium difluorotrimethylsilicate
TBAF
tetrabutylammonium fluoride
TEA
triethylamine
TEBA or TEBAC
triethylbenzylammonium chloride
TEBAC or TEBA
triethylbenzylammonium chloride
TESH
triethylsilane
Tf
trifluoromethanesulfonyl
TFA
trifluoroacetic acid
TFAA
trifluoroacetic anhydride
TFMSA or TfOH
trifluoromethanesulfonic acid
TfOH or TFMSA
trifluoromethanesulfonic acid
THF
tetrahydrofuran
THP
tetrahydropyran
TMEDA
N,N,N″,N″
-tetramethylethylenediamine
TMOF
trimethyl orthoformate
TPAP
tetrapropylammonium perruthenate
TPP
tetraphenylporphyrin
TPPTS
sulfonated triphenylphosphine
TPS
triisopropylbenzensulfonyl chloride
Tr
+
BF
4
−
or Ph
3
C
+
BF
4
−
triphenylcarbenium tetrafluoroborate
TrS
−
Bu
4
N
+
tetrabutylammonium triphenylmethanethiolate
Ts
toluenesulfonyl
