Design of chemical glycosyl donors: does changing ring conformation influence selectivity/reactivity?

This tutorial review focuses on the design of glycosyl donors, especially on attempts to control selectivity/reactivity by employing bulky substituents, cyclic protecting groups, or bridged structures. These structural modifications are performed to change the conformational distributions of pyranos...

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Bibliographic Details
Published in:Chemical Society reviews 2013-05, Vol.42 (10), p.4297-4309
Main Authors: Satoh, Hiroko, Manabe, Shino
Format: Article
Language:English
Subjects:
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Carbohydrate Conformation
Glycosides - chemistry
Glycosylation
Natural products
Readers
Selectivity
Stereoisomerism
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Summary:This tutorial review focuses on the design of glycosyl donors, especially on attempts to control selectivity/reactivity by employing bulky substituents, cyclic protecting groups, or bridged structures. These structural modifications are performed to change the conformational distributions of pyranoside/furanoside rings. We also briefly discuss this issue with regard to studies on furanosides and enzymatic glycosylation reactions. Readers will find that some of the designed glycosyl donors have been used to achieve total syntheses of natural products.
ISSN:0306-0012
1460-4744
DOI:10.1039/c3cs35457a