Application of the Wharton Rearrangement for the de novo Synthesis of Pyranosides with ido, manno, and colito Stereochemistry

A de novo asymmetric synthesis of α‐ido‐pyranosides, as well as several deoxy and amino variants, has been achieved. The procedure involves a palladium(0)‐catalyzed glycosylation in combination with a Wharton rearrangement/epoxide‐opening reaction sequence to access sugars with ido, manno, and colit...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-05, Vol.2013 (15), p.3067-3075
Main Authors: Cuccarese, Michael F., Wang, Hua-Yu Leo, O'Doherty, George A.
Format: Article
Language:English
Subjects:
Carbohydrates
Epoxides
Glycosylation
Palladium
Rearrangement
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Summary:A de novo asymmetric synthesis of α‐ido‐pyranosides, as well as several deoxy and amino variants, has been achieved. The procedure involves a palladium(0)‐catalyzed glycosylation in combination with a Wharton rearrangement/epoxide‐opening reaction sequence to access sugars with ido, manno, and colito stereochemistry as well as several azido analogues. A de novo asymmetric synthesis of α‐ido‐pyranosides, as well as several deoxy and amino variants, has been achieved. The procedure involves a palladium(0)‐catalyzed glycosylation in combination with a Wharton rearrangement/epoxide‐opening reaction sequence to access sugars with ido, manno, and colito stereochemistry as well as several azido analogues.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300051