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Synlett 1995; 1995(12): 1271-1273
DOI: 10.1055/s-1995-5254
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An Attempt at the Direct Construction of 2-Deoxy-β-glycosidic Linkages Capitalizing on 2-Deoxyglycopyranosyl Diethyl Phosphites as Glycosyl Donors

Shun-ichi Hashimoto* , Ai Sano, Hiroki Sakamoto, Makoto Nakajima, Yuki Yanagiya, Shiro Ikegami
  • *Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060, Japan
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Publication History

Publication Date:
31 December 2000 (online)

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A direct method for the construction of 2-deoxy-β-glycosidic linkages has been developed by using 2-deoxyglycopyranosyl diethyl phosphites without neighboring group substituents at C-2 as glycosyl donors in the presence of a catalytic amount of trimethylsilyl triflate (TMSOTf), wherein glycosidations of 2-deoxy-D-gluco- and 2-deoxy-L-rhamnopyranosyl donors with primary alcohols have been found to exhibit the highest β-selectivity known to date.

2-deoxyglycosyl phosphite - glycosidation - 2-deoxy-β-glycoside - trimethylsilyl triflate