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

• Published in: Chemical & Pharmaceutical Bulletin Vol. 53; no. 8; pp. 1058 - 1061
• Main Authors: Eiji KAWAHARAa, b, Mikio FUJIIc, Keisuke KATOa, Yoshiteru IDAc, Hiroyuki AKITAa
• Format: Journal Article
• Language: Japanese
• Published: Pharmaceutical Society of Japan 01.08.2005
• ISSN: 0009-2363; 1347-5223

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 bromide (15) afforded 10, 14, and 16, respectively, as coupled products. Deprotection of 10, 14, and 16 provided the synthetic benzyl β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (2), benzyl α-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside (3), and benzyl α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (4), respectively.