AN EXTREMELY MILD AND GENERAL METHOD FOR THE CONSTRUCTION OF 1, 2-TRANS-β-GLYCOSIDIC LINKAGES VIA GLYCOPYRANOSYL DIETHYL PHOSPHITES WITH PARTICIPATING GROUPS AT C-2

Shun-ichi HASHIMOTO; Ai SANO; Kazuhiro UMEO; Makoto NAKAJIMA; Shiro IKEGAMI

doi:10.1248/cpb.43.2267

Shun-ichi HASHIMOTO, Ai SANO, Kazuhiro UMEO, Makoto NAKAJIMA, Shiro IKEGAMI

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Keywords: glycosidation, 1, 2-trans-glycosidic linkage, neighboring group participation, glycosyl phosphite

JOURNAL FREE ACCESS

1995 Volume 43 Issue 12 Pages 2267-2269

DOI https://doi.org/10.1248/cpb.43.2267

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Abstract

A highly efficient 1, 2-trans-β-glycosidation reaction has been developed by using glycopyranosyl diethyl phosphites bearing participating groups such as benzoate, phthalimido, or trichloroethyl carbamate groups at C-2 as glycosyl donors and trimethylsilyl trifluoromethanesulfonate (TMSOTf) as a promoter.

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