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Communication | Special issue | Vol 77, No. 2, 2009, pp.843-848
Published online, 14th October, 2008
DOI: 10.3987/COM-08-S(F)108
Direct and Stereoselective Synthesis of 2-Azido-2-deoxy-β-D-mannosides Using the Phosphate Method

Seiichi Nakamura, Toshifumi Tsuda, Noritoshi Suzuki, and Shunichi Hashimoto*

*Laboratory of Synthetic and Industrial Chemistry, Graduate School of Life Science, Division of Life Science, Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12, Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

TMSOTf-promoted glycosidation of 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannosyl diphenyl phosphate with a variety of acceptor alcohols in CH2Cl2 at –30 °C in the presence of pulverized 4-Å molecular sieves (MS) afforded 2-azido-2-deoxy-β-mannosides in high yields and with good to high β-selectivities.