Greene's Protective Groups in Organic Synthesis (eBook)

Peter G. M. Wuts (Autor)

eBook Download: EPUB

2025 | 6. Auflage
Wiley (Verlag)
9781394233182 (ISBN)

Infos

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, 6^th 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.

Peter G. M. Wuts, PhD, is a renowned organic chemist, currently working as a chemistry consultant for both the biotech and the legal community. He continues a 50-year career in academia and the pharmaceutical industry.

Textauszug

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

BtSE	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...

Produkt-Details

• Erscheint lt. Verlag: 4.4.2025
• Sprache: englisch
• Themenwelt: Naturwissenschaften ► Chemie ► Organische Chemie
• Schlagworte: Acid • Alcohol • Alkyne • Amide • Amine • carbohydrate chemistry • Catechol • cyclic acetal • Diol • Ester • Ether • ketal • Ketone • monoprotection of dicarbonyl compound • Phenol • Phosphate • Protective group in organic synthesis • Thiol
• ISBN-13: 9781394233182 / 9781394233182