Chemoenzymatic Synthesis of Naturally Occurring Benzyl 6-O-Glycosyl-β-D-glucopyranosides

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概要

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

• 公益社団法人日本薬学会の論文
• 2005-08-01

著者

• Fujii Mikio

  School Of Pharmaceutical Sciences Showa University

• IDA Yoshiteru

  School of Pharmaceutical Sciences, Showa University

• AKITA Hiroyuki

  School of Pharmaceutical Science, Toho University

• Kato Keisuke

  Fac. Of Pharmaceutical Sciences Toho Univ.

• Akita H

  Toho Univ. Chiba Jpn

• Akita Hiroyuki

  School Of Pharmaceutical Science Toho University

• Ida Yoshiteru

  School Of Pharmaceutical Sciences Showa University

• Ida Yoshiteru

  Yokohama College Of Pharmacy

• Kato Keisuke

  School Of Pharmaceutical Sciences Toho University

• KAWAHARA Eiji

  School of Pharmaceutical Sciences, Toho University

• Kawahara Eiji

  School Of Pharmaceutical Sciences Toho University:tsukuba Research Institute Novartis Pharma K.k.

• Akita Hiroyuki

  School Of Parmaceutical Sciences Toho University

• Kato Keisuke

  School Of Pharmaceutical Science Toho University

• Ida Yoshiteru

  School Of Pharmacy Showa University:yokohama College Of Pharmacy

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