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Note | Regular issue | Vol 65, No. 6, 2005, pp.1461-1470
Published online, 24th March, 2005
DOI: 10.3987/COM-05-10383
Chemoenzymatic Synthesis of Naturally Occurring Phenethyl (1→6)-β-D-Glucopyranosides

Eiji Kawahara, Miho Nishiuchi, Mikio Fujii, Keisuke Kato, Yoshiteru Ida, and Hiroyuki Akita*

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan

Abstract

Direct β-glucosidation between phenethyl alcohol and D-glucose (5) using the immobilized β-glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave a phenethyl β-D-glucoside (1) in 34% yield. The coupling of the phenethyl O-β-D-glucopyranoside congener (8) and methylthio-2,3,4-tri-O-acetyl-β-D-xylopyranoside (9), 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide (11), and methylthio 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside (13) afforded the coupled products (10, 12, and 14), respectively. Deprotection of the coupled products (10, 12, and 14) afforded the synthetic phenethyl O-β-D-xylopyranosy-(1→6)-β-D-glucopyranoside (2), phenethyl O-α-L-arabinopyranosy-(1→6)-β-D-glucopyranoside (3), and phenethyl O-α-L-rhamnopyranosy-(1→6)-β-D-glucopyranoside (4), respectively.