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Reactions at Oxygen Atoms

  • Reference work entry
Glycoscience

Abstract

Synthetic protocols based on carbohydrates require the differentiation of their abundant hydroxyl groups, by and large, in order to expose just one single hydroxyl group to the selected reagent. This differentiation is usually carried out with the assistance of protecting groups that block the rest of the hydroxyl groups while being compatible with the given reaction conditions. By corollary, the knowledge and apt choice of the appropriate protecting groups is a key factor in successful synthetic endeavors. In this chapter, an overview of the most commonly employed protecting groups in carbohydrate chemistry is given. Alkyl ethers, being robust protecting groups, have a long history in synthetic carbohydrate chemistry and in related structural studies of polysaccharides. Acetals and ketals, which are of fundamental importance in carbohydrate chemistry, are then discussed. Acyl and silyl protecting groups, which also play an important role in modern monosaccharide transformations, are also presented. Finally, recent blocking strategies are described, including orthogonal strategies, by which the protecting groups are harmoniously combined in modern carbohydrate chemistry.

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Abbreviations

ADMB:

4‑acetoxy-2,2‑dimethylbutanoyl

All:

allyl

Alloc or Aloc:

allyloxycarbonyl

APAC:

2-(allyloxy) phenyl acetyl

BDA:

butane 2,3‑diacetals

Bn:

benzyl

Bocdene:

2-(tert-butoxycarbonyl)-ethylidene

BOM:

benzyloxymethyl ether

Bz:

benzoyl

BzOBT:

1-N-benzyloxy-1,2,3‑benzotriazol

Cac or ClAc:

chloroacetyl

CAN:

ceric ammonium nitrate

CBz:

benzyloxycarbonyl

CDA:

cyclo-hexane-1,2‑diacetal

CSA:

camphorsulfonic acid

CCL:

Candida cylindracea lipase

CVL:

Chromobacterium viscosum lipase

DABCO:

diazabicyclo[2.2.2]octane

DBMP:

ditertbutylmethylpyridine

DBU:

1,8‑diazabicyclo[5,4,0]undec-7-ene

DCC:

dicyclohexylcarbodiimide

DDQ:

dichlorodicyanoquinone

DIB:

(diacetoxyiodo)benzene

DISAL:

3,5-dinitrosalicylate

Dispoke:

dispiroketal

DMAP:

4-(dimethylamino)pyridine

DME:

dimethoxyethane

DMF:

N,N‑dimethylformamide

DMSO:

dimethylsulfoxide

DMTr:

dimethoxytriphenylmethyl

DMTST:

dimethyl(methylthio)sulfonium trifluoromethane sulfonate

DTBMP:

di-tert-butylmethylpyridine

DTBS:

ditertbutylsilylene

EDAC:

1-[3-(dimethylamino)propyl]-3‑ethylcarbodiimide hydrochloride

Fmoc:

fluoren-9‑ylmethoxycarbonyl

HATU:

2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3‑tetramethyluronium hexafluorophosphate

IDCP:

iodonium di-sym-collidine perchlorate

Lev:

levulinoyl

MEM:

methoxyethoxymethyl

MMTr:

monomethoxytriphenylmethyl

Mocdene:

2-(methoxycarbonyl)-ethylidene

MOM:

methoxymethyl ether

NAP:

2‑naphthylmethyl

NBS:

N-bromosuccinimide

NIS:

N-iodosuccinimide

NMO:

N-methylmorpholine-N-oxide

NMR:

nuclear magnetic resonance

NPM:

p-nitrophenylmethyl

PAB:

pivaloylaminobenzyl

PBB:

p-bromobenzyl

PCB:

p-chlorobenzyl

PFL:

Pseudomonas fluorescens lipase

Piv:

pivaloyl

PIB:

p-iodobenzyl

PLE:

pig liver esterase

PMB:

p-methoxybenzyl

PMBM:

p-methoxybenzyloxymethyl

PN:

protease N‑neutral protease

Poc:

propargyloxycarbonyl

PPL:

lipase from porcine pancreas

PPTS:

pyridinium p-toluenesulfonate

PSE:

phenylsulfonylethylidene

RJL:

Rhizopus javanicus lipase

SEE:

1-[2-(trimethylsilyl)ethoxy]ethyl

SEM:

trimethylsilylethoxymethyl ether

SET:

single electron transfer

TBS or TBDMS:

tert-butyldimethylsilyl

TBDPS:

tert-butyldiphenylsilyl

TES:

triethylsilyl

TFA:

trifluoroacetic acid

TFAA:

trifluoroacetic anhydride

THF:

tetrahydrofurane

TIBAL:

triisobutylaluminum

TIPDS:

1,1,3,3‑tetraisopropyldisiloxane

TIPS:

trisopropylsilyl

TMEDA:

tetramethylethylenediamine

TMS:

trimethylsilyl

TMTr:

trimethoxytriphenylmethyl

TPS:

triphenylsilyl

Tr:

trityl

Troc:

2,2,2‑trichloroethyloxycarbonyl

TBAF:

tetrabutylammonium fluoride

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Acknowledgement

A.M.G. is grateful to the Ministerio de Educación y Ciencia of Spain [CTQ2006–15279-CO3–02/BQU] for financial support.

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Authors and Affiliations

  1. Instituto de Química Orgánica General, (CSIC), 28006, Madrid, Spain

    Ana M. Gómez

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  1. Ana M. Gómez
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Editors and Affiliations

  1. Natural Products and Glycotechnology Research Institute Inc., North Caroline State University, 4118 Swarthmore Road, Durham, NC, 27707, USA

    Bertram O. Fraser-Reid Prof. Dr.

  2. University Graduate School of Science and Engineering, 3-4-1 Ohkubo, Shinjuku, Tokyo, Japan

    Kuniaki Tatsuta Prof. Dr.

  3. Faculty of ScienceDepartment of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany

    Joachim Thiem Prof. Dr.

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Gómez, A. (2008). Reactions at Oxygen Atoms. In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_3

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