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Synthesis of Benzyl 2-Deoxy-C-Glycosides. 2020

Tsuyoshi Shinozuka
R&D Planning & Management Department, R&D Division, Daiichi Sankyo Company Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan.

A synthetic method for benzyl 2-deoxy-C-glycosides has been developed. Palladium-catalyzed benzyl C-glycosylation of TIPS-protected 1-tributylstannyl glycals with a variety of benzyl bromides provided protected benzyl C-glycals. In this reaction, the use of PdCl2(dppe) promoted a clean reaction, whereas the reaction was accelerated by the addition of Na2CO3. The subsequent transformations provided a novel class of benzyl 2-deoxy-C-glycosides.

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