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Paper | Regular issue | Vol 65, No. 9, 2005, pp.2127-2137
Published online, 8th July, 2005
DOI: 10.3987/COM-05-10474
Chemoenzymatic Synthesis of Naturally Occurring (Z)-3-Hexenyl 6-O-Glycosyl-β-D-glucopyranosides

Masashi Kishida, Mikio Fujii, 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 cis-3-hexen-1-ol and D-glucose (5) using the immobilized β-glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave (Z)-3-hexenyl β-D-glucoside (1) in 17% yield. The coupling of the (Z)-3-hexenyl O-β-D-glucopyranoside congener (7) with 2,3,4-tri-O-benzoyl-α-D-xylopyranosylÅ@bromide (8) gave the coupled product (11). Similarly the coupling of 7 with 2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl bromide (9), and that of 7 with 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide (10) afforded the coupled products (12 and 13), respectively. Deprotection of the products (11, 12, and 13) afforded (Z)-3-hexenyl O-β-D-xylopyranosyl-(1Å®6)-β-D-glucopyranoside (2), (Z)-3-hexenyl O-α-L-arabinopyranosyl-(1Å®6)-β-D-glucopyranoside (3), and (Z)-3-hexenyl O-α-L-rhamnopyranosyl- (1Å®6)-β-D-glucopyranoside (4), respectively.