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Access to ring-expanded analogues of 2-amino sugars.

Authors
  • Saha, Jaideep
  • Peczuh, Mark W
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Oct 01, 2009
Volume
11
Issue
19
Pages
4482–4484
Identifiers
DOI: 10.1021/ol9018387
PMID: 19722606
Source
Medline
License
Unknown

Abstract

Ring-expanded 2-N-acetylamino sugar analogs of D-glucose, D-galactose, and D-mannose have been prepared by a new synthetic route. Aspects of the highly substituted alpha-amino aldehyde intermediates made them central to the approach. First, they were accessed via diastereoselective addition of a vinyl Grignard onto protected glycosyl amines. Also, the sterics of the bis-protected amine favored the formation of only one glycoside anomer. The new analogues reported here should prove useful in the development of tools to investigate the role of 2-amino sugars in biology.

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