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Paper | Special issue | Vol 61, No. 1, 2003, pp.459-470
Published online, 4th November, 2003
DOI: 10.3987/COM-03-S60
Stereospecific Access to β-Mannosides from Glucose-derived 1,2-Orthoesters as Glycosyl Donors

Eisuke Kaji,* Yugo Hosokawa, Yusuke Watanabe, Mina Kobayashi, and Mayumi Yamakawa

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


A new, stereospecific synthesis of β-mannosides from glucose-derived 1,2-orthoesters has been developed by a simple four step procedure, comprising β-specific glycosidation of the 1,2-orthoesters, 2’-O-deacetylation, 2’-O-triflation, and SN 2 type inversion of the triflyl group providing β-D-Man-(1→6)-D-Gal, and β-D-Man-(1→4)-D-Glc derivatives in reasonable yield.