Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Chemoenzymatic Synthesis of n-Hexyl and O-β-D-Xylopyranosyl-(1→6)-β-D-glucopyranosides
Masashi KishidaMiho NishiuchiKeisuke KatoHiroyuki Akita
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2004 年 52 巻 9 号 p. 1105-1108

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Direct β-glucosidation between 1,6-octanediol (5) and D-glucose (3) using the immobilized β-glucosidase (EC 3.2.1.21) from almonds with the synthetic prepolymer ENTP-4000 gave a mono-β-glucoside (6) in 61.4% yield, which was converted into the n-hexyl β-D-glucopyranoside (1) by means of a chemoenzymatic method. The coupling of the n-hexyl β-D-glucopyranoside congener (13) and 2,3,4-tri-O-acetyl-β-D-xylosyl congener (14), followed by deprotection, afforded the synthetic n-hexyl O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (2), which was identical to the natural 2 with respect to the spectral data and specific rotation.

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© 2004 The Pharmaceutical Society of Japan
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