Glycosidation Reactions of Silyl Ethers with Conformationally Inverted Donors Derived from Glucuronic Acid: Stereoselective Synthesis of Glycosides and 2-Deoxyglycosides

The donor makes the difference: The tin(IV) chloride catalyzed coupling of silyl ethers to donors derived from glucuronic acid has shown that the silyl ethers (see scheme) are significantly better acceptors than the corresponding alcohols or phenol. The reactions are highly stereoselective and depen...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2004-05, Vol.43 (19), p.2518-2521
Main Authors: Poláková, Monika, Pitt, Nigel, Tosin, Manuela, Murphy, Paul V.
Format: Article
Language:English
Subjects:
carbohydrates
glucuronic acid
Glucuronic Acid - chemistry
glycosides
Glycosides - chemical synthesis
Glycosylation
Organosilicon Compounds - chemistry
Stereoisomerism
stereoselective synthesis
Tin Compounds - chemistry
Trimethylsilyl Compounds - chemistry
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Summary:The donor makes the difference: The tin(IV) chloride catalyzed coupling of silyl ethers to donors derived from glucuronic acid has shown that the silyl ethers (see scheme) are significantly better acceptors than the corresponding alcohols or phenol. The reactions are highly stereoselective and dependant on the donor structure. They provide 1,2‐trans‐ and 1,2‐cis‐(deoxy)glycosides in moderate to excellent yields.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200353196