Chemoenzymatic synthesis of naturally occurring benzyl 6-O-glycosyl-beta-D-glucopyranosides.

Abstract:

:Direct beta-glucosidation between benzyl alcohol and D-glucose (5) using the immobilized beta-glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave a benzyl beta-D-glucoside (1) in 53% yield. The coupling of the benzyl beta-D-glucopyranoside congener (8) derived from 1 with phenyl 2,3,4-tri-O-acetyl-1-thio-beta-D-xylopyranoside (9), ethyl 2,3,4-tri-O-acetyl-1-thio-alpha-L-rhamnopyranoside (13), and 2,3,4-tri-O-acetyl-alpha-L-arabinopyranosyl bromide (15) afforded 10, 14, and 16, respectively, as coupled products. Deprotection of 10, 14, and 16 provided the synthetic benzyl beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside (2), benzyl alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (3), and benzyl alpha-L-arabinopyranosyl-(1-->6)-beta-D-glucopyranoside (4), respectively.

authors

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

doi

10.1248/cpb.53.1058

subject

Has Abstract

pub_date

2005-08-01 00:00:00

pages

1058-61

issue

8

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/53.1058

journal_volume

53

pub_type

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