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Communication | Special issue | Vol 52, No. 2, 2000, pp.579-582
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S100
Expedient Stereospecific Synthesis of β-Mannosides from a Glucose-derived 1,2-Orthoester

Eisuke Kaji* and Yugo Hosokawa

*School of Pharmaceutical Sciences, Kitasato University, Shirokane 5-9-1, Minato-ku, Tokyo 108-8641, Japan

Abstract

A new, stereospecific synthesis of β-mannosides from glucose-derived 1,2-orthoester has been developed using a simple four-step procedure. For the synthesis of β-D-Man-(1→6)-D-Gal, a 6-OH free galactose derivative was glycosylated with the orthoester to yield β-D-Glc-(1→6)-D-Gal; the Glc unit of which was epimerized into the β-mannoside in good yield.