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本文合成了辣椒素类物质-4-O-β-D-葡萄糖苷类化合物(3)。首先,以BF3·OEt2为催化剂,用五乙酰葡萄糖酯与辣椒素类物质反应得到中间体辣椒素类物质-4-O-β-D-四乙酰葡萄糖苷类化合物(2),以硅胶柱色谱纯化收率为22%,LC-MS分析表明含有降二氢辣椒素四乙酰葡萄糖苷(2a,M623)、辣椒素四乙酰葡萄糖苷(2b,M635)、二氢辣椒素四乙酰葡萄糖苷(2c,M637)、高二氢辣椒素四乙酰葡萄糖苷(2d,M651);中间体2易水解为目标化合物3,收率63%。1HNMR分析表明化合物2及3均为β构型。
In this paper, capsaicin -4-O-β-D-glucoside compound (3) was synthesized. First, the intermediate capsaicin-4-O-β-D-tetraacetylglucoside compound (2) was synthesized by the reaction of pentacetylglucose ester and capsaicinoid with BF3 · OEt2 as catalyst. The residue was purified by silica gel column chromatography The purification yield was 22%. LC-MS analysis showed that the compound containing the prothiocarbamide tetraacetylglucoside (2a, M623), capsaicin tetraacetylglucoside (2b, M635), dihydrotestosterone tetraacetylglucoside , M637) and high dihydrotestosterone tetraacetylglucoside (2d, M651). The intermediate 2 was hydrolyzed to the target compound 3 in 63% yield. 1H NMR analysis showed that both compounds 2 and 3 were in beta configuration.