Direct β-glucosidation between cis-3-hexen-1-ol and D-glucose (5) using the immobilized β-glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave (Z)-3-hexenyl β-D-glucoside (1) in 17% yield. The coupling ofthe (Z)-3-hexenyl O-β-D-glucopyranoside congener (7) with 2,3,4-tri-O-benzoyl-α-D-xylopyranosyl bromide (8) gave the coupled product (11). Similarly the coupling of 7 with 2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl bromide (9), and that of 7 with 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide (10) afforded the coupled products (12 and 13), respectively. Deprotection of the products (11, 12, and 13) afforded (Z)-3-hexenyl O-β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranoside (2), (Z)-3-hexenyl O-α-L-arabinopyranosyl-(1→6)-βp-D-glucopyranoside (3), and (Z)-3-hexenyl O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (4), respectively.

中文翻译：

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天然存在的 (Z)-3-己烯基 6-O-糖基-β-D-吡喃葡萄糖苷的化学酶合成

使用来自杏仁的固定化 β-葡萄糖苷酶与合成预聚物 ENTP-4000 直接 β-葡萄糖苷化 cis-3-hexen-1-ol 和 D-葡萄糖 (5)，得到 (Z)-3-己烯基 β-D-葡萄糖苷 ( 1) 产率为 17%。(Z)-3-己烯基 O-β-D-吡喃葡萄糖苷同系物 (7) 与 2,3,4-三-O-苯甲酰基-α-D-吡喃木糖基溴 (8) 偶联得到偶联产物 (11) . 类似地，7 与 2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl bromide (9) 的偶联，以及 7 与 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl 的偶联溴化物 (10) 分别提供偶联产物 (12 和 13)。将产物 (11、12 和 13) 脱保护得到 (Z)-3-己烯基 O-β-D-吡喃木糖基-(1 → 6)-β-D-吡喃葡萄糖苷 (2), (Z)-3-己烯基O-α-L-阿拉伯吡喃糖基-(1→6)-βp-D-吡喃葡萄糖苷(3)和(Z)-3-己烯基O-α-L-吡喃鼠李糖基-(1→6)-β-D-吡喃葡萄糖苷(4) 分别。