Potent, Versatile, and Stable: Thiazolyl Thioglycosides as Glycosyl Donors

Donating with a difference: Thiazolyl (Taz) substituted thioglycosides have been successfully used in the synthesis of both 1,2‐trans‐ and 1,2‐cis‐glycosides and also have found application in convergent oligosaccharide synthesis. In addition, this study has demonstrated that STaz and SEt moieties a...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2004-06, Vol.43 (23), p.3069-3072
Main Authors: Demchenko, Alexei V., Pornsuriyasak, Papapida, De Meo, Cristina, Malysheva, Nelli N.
Format: Article
Language:English
Subjects:
carbohydrates
chemoselectivity
glycosides
Glycosylation
Stereoisomerism
Thiazoles - chemistry
Thioglycosides - chemical synthesis
Thioglycosides - chemistry
Thioglycosides - metabolism
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Summary:Donating with a difference: Thiazolyl (Taz) substituted thioglycosides have been successfully used in the synthesis of both 1,2‐trans‐ and 1,2‐cis‐glycosides and also have found application in convergent oligosaccharide synthesis. In addition, this study has demonstrated that STaz and SEt moieties are fully orthogonal (see scheme, Bn=benzyl; X=STaz, Y=SEt or X=SEt, Y=STaz).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200454047