Brønsted Acid-Promoted Glycosylations of Disaccharide Glycal Substructures of the Saccharomicins

• Authors: Bradley R. Balthaser, Emory University; Frank McDonald, Emory University
• Journal Title: Organic Letters
• Volume: Volume 11, Number 21
• Publisher: American Chemical Society | 2009-11-05, Pages 4850-4853
• Type of Work: Article | Post-print: After Peer Review
• Publisher DOI: http://doi.org/10.1021/ol901923x
• Subjects: Chemistry, General

Abstract

An acid-promoted glycosylation and alkynol cycloisomerization sequence provided direct access to the 2-deoxytrisaccharide corresponding to the fucose-saccharosamine-digitoxose substructure of saccharomicin B. In the course of this work, the absolute stereochemistry of the repeating fucose-saccharosamine disaccharide of saccharomicins was also confirmed.