8-氧-叔丁基二甲基硅烷基-4,5-氧-羰基-3-去氧-β-D-甘露-2-辛酮糖甲酸酯烯丙基苷的合成  

Synthesis of methyl( allyl 8-O-tert-butyldimethylsilyl-4,5-O-carbonyl-3-deoxy-β-D-mano-2-octulopyranosid) onate

作　　者：王鑫 杨劲松[1] 

机构地区：[1]四川大学华西药学院,四川成都610041

出　　处：《华西药学杂志》2017年第5期449-451,共3页West China Journal of Pharmaceutical Sciences

基　　金：国家自然科学基金资助项目(批准号:21572145)

摘　　要：目的研究8-氧-叔丁基二甲基硅烷基-4,5-氧-羰基-3-去氧-β-D-甘露-2-辛酮糖甲酸酯烯丙基苷的合成。方法以草酰乙酸和D-阿拉伯糖为原料,通过cornforth反应、乙酰化、甲酯化、烯醇化、脱乙酰基、硅基化、碳酸酯化等7步反应制备目标化合物。结果与结论与文献谱图进行对照,确证目标化合物的结构,7步反应的总收率为22%,化合物的立体选择性较高,方法操作简单、易于实施,为含(2→7)苷键结构的Kdo寡糖制备奠定了基础。OBJECTIVE To investigate a practical and convenient method to synthesize methyl（ allyl 8-O-tert-butyldimethylsilyl-4,5-O-carbonyl-3-deoxy-β-D-mano-2-octulopyranosid） onate. METHODS The target compound was synthesized using oxaloacetic acid and D-arabinose by cornforth reaction,acetylation,methylesterification,enolization,deacetylation,silylation and carbonation. RESULTS and CONCLUSION The structure of the target compound was confirmed by comparing1 HNMR data with the known compound. The total yield after seven steps was 22%. Furthermore,the synthetic compound 7 can be used in the synthesis of oligosaccharide containing（ 2→7） Kdo-Kdo dimer structure.

关 键 词：8-氧-叔丁基二甲基硅烷基-4 5-氧-羰基-3-去氧-β-D-甘露-2-辛酮糖甲酸酯烯丙基苷 D-阿拉伯糖 Kdo受体 Cornforth反应 Kdo寡糖 立体选择性 合成 

分 类 号：R914[医药卫生—药物化学]