Chemoenzymatic Synthesis of Naturally Occurring Benzyl 6-O-Glycosyl-. BETA.-D-glucopyranosides

E Kawahara, M Fujii, K Kato, Y Ida, H Akita

Index: Kawahara, Eiji; Fujii, Mikio; Kato, Keisuke; Ida, Yoshiteru; Akita, Hiroyuki Chemical and Pharmaceutical Bulletin, 2005 , vol. 53, # 8 p. 1058 - 1061

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Citation Number: 12

Abstract

Direct β-glucosidation between benzyl alcohol and D-glucose (5) using the immobilized β- glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave a benzyl β-D- glucoside (1) in 53% yield. The coupling of the benzyl β-D-glucopyranoside congener (8) derived from 1 with phenyl 2, 3, 4-tri-O-acetyl-1-thio-β-D-xylopyranoside (9), ethyl 2, 3, 4-tri- O-acetyl-1-thio-α-L-rhamnopyranoside (13), and 2, 3, 4-tri-O-acetyl-α-L-arabinopyranosyl ...