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

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

doi:10.1039/b925587g

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

Org Biomol Chem. 2010 Mar 7;8(5):988-90. doi: 10.1039/b925587g. Epub 2010 Jan 7.

Authors

Shunichi Kusumi¹, Sainan Wang, Tatsuya Watanabe, Kaname Sasaki, Daisuke Takahashi, Kazunobu Toshima

Affiliation

¹ Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

PMID: 20165785
DOI: 10.1039/b925587g

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.