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Study of the Glycosidation Properties of 1-Thiomannosazidopyranosides and 1-Thiomannosaziduronic Acid Esters

✍ Scribed by Leendert J. van den Bos; Boudewijn A. Duivenvoorden; Martijn C. de Koning; Dmitri V. Filippov; Herman S. Overkleeft; Gijsbert A. van der Marel

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
180 KB
Volume
2007
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

A study of the glycosylation properties of 1‐thiomannosazides with a variety of electron‐withdrawing substituents in combination with the Ph~2~SO/Tf~2~O and NIS/TMSOTf reagent systems is presented. Further, assembly of the fully protected trisaccharide 26, which corresponds to the repeating unit of the enterobacterial common antigen, using both an orthogonal and a chemoselective coupling strategy and based on the outcome of our glycosylation studies, is discussed. (Β© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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