Glycosylation Using Diphenylphosphinate as a New Leaving Group

Jun-ichi KADOKAWA*, Jun EBANA, Takeshi NAGAOKA, Masa KARASU, Hideyuki TAGAYA and Koji CHIBA

Department of Materials Science and Engineering, Faculty of Engineering, Yamagata University; Yonezawa-shi 992-8510 Japan

In this study, glycosylation using diphenylphosphinate as a new leaving group was examined. When the glycosylation of various alcohols with acetylated β-D-glucopyranosyl diphenylphosphinate (1) was carried out in the presence of trimethylsilyl trifluoromethanesulfonate in nitromethane, both the corresponding glucosides and the glucosides, which were deacetylated at position 2, were produced. Three kinds of reaction paths through an ortho ester intermediate can be considered for the present glycosylation.

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