Chemoenzymatic Synthesis of n-Hexyl and O-β-D-Xylopyranosyl-(1→6)-β-D-glucopyranosides

• Published in: Chemical & Pharmaceutical Bulletin Vol. 52; no. 9; pp. 1105 - 1108
• Main Authors: Masashi KISHIDAa, b, Miho NISHIUCHIa, Keisuke KATOa, Hiroyuki AKITAa
• Format: Journal Article
• Language: Japanese
• Published: Pharmaceutical Society of Japan 01.09.2004
• ISSN: 0009-2363; 1347-5223

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.