Multi-Step Organic Synthesis E-Book

Nicolas Bogliotti

• Herausgeber: Wiley-VCH Verlag GmbH & Co. KGaA
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 252

Veröffentlichungsjahr: 2017

Beschreibung

Combining theoretical knowledge of synthetic transformations, practical considerations, structural elucidation by interpretation of spectroscopic data as well as rationalization of structure-property relations, this textbook presents a series of 16 independent exercises, including detailed descriptions of experimental procedures, questions, and answers. The experimental descriptions are very helpful for guiding less experienced students towards a better understanding of practical aspects in synthetic organic chemistry, while the broad scope of the questions and answers is excellent for learning purposes. The exercises are based on published research articles, adapted for didactic purposes, and will thus inspire students by way of having to solve real-life problems in chemistry.
A must-have for MSc and PhD students as well as postdocs in organic chemistry and related disciplines, and lecturers and organizers of lab courses in organic chemistry.

Leseprobe

Multi-Step Organic Synthesis

A Guide Through Experiments

Nicolas Bogliotti and Roba Moumné

Authors

Dr. Nicolas Bogliotti

PPSM, ENS Paris-Saclay

CNRS, Université Paris-Saclay

94235 Cachan

France

Dr. Roba Moumné

Sorbonne Universités

UPMC Univ. Paris 06

École normale supérieure

PSL Research University

CNRS, Laboratoire des Biomolécules (LBM)

4 Place Jussieu

75005 Paris

France

All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate.

Library of Congress Card No.: applied for

British Library Cataloguing-in-Publication Data

A catalogue record for this book is available from the British Library.

Bibliographic information published by the Deutsche Nationalbibliothek

The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at http://dnb.d-nb.de.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany

All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form – by photoprinting, microfilm, or any other means – nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law.

Print ISBN: 978-3-527-34065-1

ePDF ISBN: 978-3-527-69898-1

ePub ISBN: 978-3-527-69899-8

Mobi ISBN: 978-3-527-69900-1

Cover Design Schulz Grafik-Design, Fußgönheim, Germany

Preface

This

List of Abbreviations

AA

amino acid

Ac

acetyl

ACE-Cl

α-chloroethyl chloroformate

AIBN

azobisisobutyronitrile

All

allyl

aq.

aqueous

Ar or ar

aryl or aromatic

Arg

arginine

Asp

aspartic acid

atm

atmosphere

a.u.

arbitrary unit

9-BBN

9-borabicyclo[3.3.1]nonane

BINOL

1,1′-bi-2-naphtol

Bip

biphenylalanine

Bn

benzyl

Boc

tert

-butoxycarbonyl

br

broad

C

cystein

ca.

circa

CAN

ceric ammonium nitrate

cat.

catalyst or catalytic

Cbz

carboxybenzyl

CBC

covalent bond classification

CDI

carbonyldiimidazole

Cha

cyclohexylalanine

ClF

4-chlorophenylalanine

COD

1,5-cyclooctadiene

conv.

conversion

Cy

cyclohexyl

D

aspartic acid

d

doublet

DAADH

D-amino acid dehydrogenase

DBU

1,8-diazabicyclo[5.4.0]undec-7-ene

DCC

N-N′

-dicyclohexylcarbodiimide

dd

doublet of doublets

de

diastereoisomeric excess

D-Glu

D-glucose

dr

diastereoisomeric ratio

DIAD

diisopropyl azodicarboxylate

DIBAL-H

diisobutylaluminium hydride

DIC

N-N′

-diisopropylcarbodiimide

DIPEA

N

,

N

-diisopropylethylamine

DMA

dimethylacetamide

DMAP

4-dimethylaminopyridine

DMBA

1,3-dimethylbarbituric acid

DMF

dimethylformamide

E

glutamic acid

F

phenylalanine

e

−

electron

EDC

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide

ee

enantiomeric excess

equiv.

equivalent

G

glycine

GDH

glucose dehydrogenase

Gly

glycine

h

hour

5-HT

5-hydroxytryptamine

HATU

1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate

HBTU

3-[bis(dimethylamino)methyliumyl]-3

H

-benzotriazol-1-oxide hexafluorophosphate

Hfe

homophenylalanine

HFIP

hexafluoroisopropanol

HMPA

hexamethylphosphoramide

HOAt

1-hydroxy-7-azabenzotriazole

HOBt

N

-hydroxybenzotriazole

HPLC

high performance liquid chromatography

HRMS

high resolution mass spectrometry

KHMDS

potassium bis(trimethylsilyl)amide

m

multiplet

IPAc

isopropyl acetate

K

lysine

L

leucine

Leu

leucine

LiHMDS

lithium bis(trimethylsilyl)amide

liq.

liquid

Lys

lysine

m

-CPBA

meta-chloroperoxybenzoic acid

MEK

methyl ethyl ketone

Mes

mesityl

MIBK

methyl isobutyl ketone

MIC

minimal inhibitory concentration

MIO

4-methylideneimidazole-5-one

MS

molecular sieves

Ms

mesyl

1-Nal

1-naphtylalanine

2-Nal

2-naphtylalanine

NADH

nicotinamide adenine dinucleotide

NADPH

nicotinamide adenine dinucleotide phosphate

NBS

N

-bromosuccinimide

NCS

N

-chlorosuccinimide

NHS

N

-hydroxysuccinimide

NIR

near infrared

Nle

norleucine

NMM

N

-methylmorpholine

NMO

N

-methylmorpholine

N

-oxide

NMP

N

-methyl-2-pyrrolidone

NMR

nuclear magnetic resonance

Np

naphtyl

P

proline

p

d-proline

Pro

proline

pro

d-proline

PAL

phenylalanine ammonia lyase

Pbf

2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl

PBS

phosphate-buffered saline

PEG

polyethylene glycol

PG

protecting group

PG-I

protegrin I

PLP

pyridoxal 5′-phosphate

PMB

4-methoxybenzyl

Pmc

2,2,5,7,8-pentamethyl-chromane-6-sulfonyl

P(

o

-Tol)

3

tri(

ortho

-tolyl)phosphine

Pp

2-phenyl-2-propyl

PTSA

para

-toluenesulfonic acid

Ph

phenyl

Phe

phenylalanine

Phg

phenylglycine

Q

glutamine

q

quartet

quant.

quantitative

R

arginine

rt

room temperature

R

f

retardation factor

RFU

relative fluorescence unit

s

singlet or second

SMO

Smoothened

soln.

solution

Su

succinimide

t

triplet

TBAF

tetra-

n

-butylammonium fluoride

TBME

tert

-butyl methyl ether

TBS

tert

-butyldimethylsilyl

TBDPS

tert

-butyldiphenylsilyl

TEMPO

2,2,6,6-tetramethylpiperidinyloxy

Tf

trifluoromethanesulfonyl

TFA

trifluoroacetic acid

THF

tetrahydrofuran

TLC

thin-layer chromatography

TMEDA

tetramethylethylenediamine

TMS

trimethylsilyl

Tol

tolyl

Ts

4-toluenesulfonyl

TSTU

2-succinimido-1,1,3,3-tetramethyluronium tetrafluoroborate

Tyr

tyrosine

UV

ultraviolet

V

valine

Val

valine

vis

visible

vs

versus

v/v

volume by volume

W

tryptophane

w/w

weight by weight

Y

tyrosine

Chapter 1Atovaquone: An Antipneumocystic Agent