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Regioselective Protection of Sugars Catalyzed by Dimethyltin Dichloride

Yosuke Demizu, Yuki Kubo, Hiroko Miyoshi, Toshihide Maki, Yoshihiro Matsumura, Noriaki Moriyama and Osamu Onomura*

*Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan, Email: onomuranagasaki-u.ac.jp

Y. Demizu, Y. Kubo, H. Miyosho, T. Maki, Y. Matusumura, N. Moriyama, O. Onomura, Org. Lett., 2008, 10, 5075-5077.

DOI: 10.1021/ol802095e (free Supporting Information)



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Abstract

Highly regioselective monoprotection of hydroxyl groups in sugars was accomplished along with high chemical yield in the presence of dimethyltin dichloride as catalyst. The regioselectivity of the benzoylation of sugars is based on a stereorelationship among their hydroxyl groups.

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Key Words

benzoylation


ID: J54-Y2008-3430