- Chemoenzymatic synthesis of naturally occurring phenethyl (1→6)-β-D-gluco-pyranosides
-
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.
- Kawahara, Eiji,Nishiuchi, Miho,Fujii, Mikio,Kato, Keisuke,Ida, Yoshiteru,Akita, Hiroyuki
-
p. 1461 - 1470
(2007/10/03)
-
- Synthesis and n.m.r. spectral properties of grape monoterpenyl glycosides
-
Several grape 6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosides and 6-O-α-L-arabinofuranosyl-β-D-glucopyranosides having (E)- and (Z)-3,7-dimethyl-2,6-octadien-1-yl, (R,S)-3,7-dimethyl-1,6-octadien-3-yl, (R,S)-1-methyl-1-(4-methyl-3-cyclohexen-1-yl)et
- Voirin, Stephane,Baumes, Raymond,Bayonove, Claude,M'Bairaroua, Oubadjim,Tapiero, Claude
-
-