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目的研究天然产物chlorogenin 3-O-β-chacotrioside(Ⅰ)苷元结构中的C6-OH对H5N1血凝素蛋白抑制活性的影响,设计合成了其结构类似物Ⅱ。方法采用逐步线性合成的策略,以薯蓣皂苷为起始原料,依次经氢化还原、糖苷化、脱Bz保护基、用Bz保护基选择性保护D-葡萄糖的3,6-OH、糖苷化、脱Bz与Ac保护基等线性6步反应制备了目标化合物。结果目标化合物Ⅱ的总收率为35.2%,其结构经NMR、Ms确证。结论以薯蓣皂苷为起始原料,经6步反应以35.2%的总收率合成了化合物Ⅰ的结构类似物Ⅱ。
Objective To study the effect of C6-OH on the hemagglutinin inhibitory activity of H5N1 in the aglycone structure of natural product chlorogenin 3-O-β-chacotrioside (Ⅰ), and its structural analogue Ⅱ was designed and synthesized. Methods The method of stepwise linear synthesis was used. Diosgenin was used as the starting material, followed by hydrogenation reduction, glycosylation and deprotection of Bz. The 3,6-OH of D-glucose was selectively protected by Bz protecting group and glycosylated Bz and Ac protective group linear 6-step reaction of the target compound. Results The total yield of target compound II was 35.2%. Its structure was confirmed by NMR and Ms. Conclusion Diosgenin was used as the starting material to synthesize the structural analogue II of compound Ⅰ in six steps with the overall yield of 35.2%.