2010•Organic & Biomolecular ChemistryRequires access

Chemoselective glycosylations using 2,3-unsaturated-4-keto glycosyl donors

Shunichi Kusumi, Sainan Wang, Tatsuya Watanabe, Kaname Sasaki, Daisuke Takahashi, Kazunobu Toshima

Abstract

2,3-Unsaturated-4-keto glycosyl acetates were found to exhibit low reactivity under several glycosylation conditions. Chemoselective glycosylations were effectively performed using 2,3-unsaturated glycosyl and 2,3-dideoxy glycosyl acetates as armed glycosyl donors, and 2,3-unsaturated-4-keto glycosyl acetates as disarmed glycosyl donors.

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Key concepts: Glycosyl, Chemistry, Glycosylation, Glycosyl donor, Reactivity (psychology), Carbohydrate synthesis, Stereochemistry, Organic chemistry