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Paper | Regular issue | Vol 68, No. 2, 2006, pp.323-330
Published online, 17th January, 2006
DOI: 10.3987/COM-05-10640
Chemoenzymatic Synthesis of Naturally Occurring Geranyl 6-O-Glycosyl-β-D-glucopyranosides

Eiji Kawahara, Mikio Fujii, Yoshiteru Ida, and Hiroyuki Akita*

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


Direct β-glucosidation between geranyl alcohol and D-glucose (4) using the immobilized β-glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave geranyl O-β-D-glucoside (1) in 11% yield. The coupling of the geranyl O-β-D-glucopyranoside congener (7) with 2,3,4-tri-O-benzoyl-α-D-xylopyranoside bromide (8) or 2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl bromide (10) afforded the coupled products (9 and 11), respectively. Deprotection of the coupled products (9 and 11) using MeONa in MeOH-THF gave the synthetic geranyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside (2) and geranyl 6-O-α-L-arabinopyranosyl-β-D-glucopyranoside (Kenposide A, 3).