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S-Glycosylation

  • Reference work entry
Glycoscience

Abstract

Published methods to synthesize thioglycosides have been reviewed. Two major pathways are recognized, either a displacement of an anomeric leaving group with a thiol acceptor to give the thioglycoside directly, or an initial formation of an anomeric thiol, which then is alkylated to give the thioglycoside. For the direct approach a listing is made based on the diverse anomeric leaving groups that have been utilized, acetates and halides being the most common. For the second pathway, various ways to form an anomeric thiol in a stereoselective manner are summarized, hydrolysis of anomeric thioacetates or pseudothiouronium salts being the most frequent, as well as different methodologies to perform the subsequent alkylation or arylation. Some miscellaneous pathways to thioglycosides, mainly through rearrangement of special O‑glycosyl derivatives, are also discussed. In the last part an overview of the use of the discussed methodologies in the synthesis of thiooligosaccharides, i. e. oligosaccharides with interglycosidic thiolinkages, is presented.

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Abbreviations

AIBN:

azobisisobutyronitrile

CAN:

ceric ammonium nitrate

DMF:

dimethylformamide

DTT:

dithiothreitol

HMPA:

hexamethylphosphoramide

IDCP:

iodonium dicollidine perchlorate

Kdo:

3-deoxy-d-manno-2-octulosonic acid

mCPBA:

meta-chloroperoxybenzoic acid

NIS:

N-iodosuccinimide

OTMS:

octadecyltrimethoxysilane

TFA:

trifluoroacetic acid

TMSO:

N-trimethylsilyl-2‑oxazolidinone

UDP:

uridine diphosphate

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Authors and Affiliations

  1. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, 106 91, Sweden

    Stefan Oscarson

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  1. Stefan Oscarson
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Editor information

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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Oscarson, S. (2008). S-Glycosylation. In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_14

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