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目的探讨立体选择性合成脑甾醇的新方法。方法以猪去氧胆酸为原料,经甲酯化、还原、Wittig反应、Sharpless不对称双羟化等9步反应合成脑甾醇,其中以乙酰链甾醇为关键中间体,以Sharpless不对称双羟化反应为关键步骤。结果以52%的总收率、97%de的立体选择性合成脑甾醇,其结构用质谱(MS)、核磁共振氢谱(1HNMR)、核磁共振碳谱(13CNMR)、红外光谱(IR)和元素分析等证实。结论新的合成方法立体选择性高、收率高、每个中间体均为晶体易于重结晶纯化,可用于大量合成脑甾醇。
Objective To explore a new method of stereoselective synthesis of sterol. Methods The synthesis of cetyl sterol was carried out in 9 steps, including methyl esterification, reduction, Wittig reaction and Sharpless asymmetric dihydroxylation, using hyodeoxycholic acid as raw material. Acetosterol was used as the key intermediate and Sharpless asymmetric dihydroxylation The reaction is a key step. Results Stereoselective stereoselective synthesis of corticosterol was achieved in 52% of total yield with 97% de and its structure was characterized by MS, 1HNMR, 13CNMR, IR and Elemental analysis confirmed. Conclusion The new synthesis method has high stereoselectivity and high yield. Each intermediate is a crystal which is easy to be recrystallized and purified, and can be used for synthesizing large quantities of cerebral sterol.