两种3,4-位环状保护基保护的半乳糖乙硫苷供体的合成  

Synthesis of two thiogalactoglycoside donors protected by 3,4-cyclic protecting groups

作　　者：徐椿云 杨劲松[1] XU Chunyun;YANG Jinsong(West China School of Pharmacy,Sichuan University,Chengdu,Sichuan,610041 P.R.China)

机构地区：[1]四川大学华西药学院

出　　处：《华西药学杂志》2019年第6期555-558,共4页West China Journal of Pharmaceutical Sciences

基　　金：国家自然科学基金资助项目(批准号:21772132)

摘　　要：目的合成3,4-位环状保护基保护的半乳糖乙硫苷供体。方法以半乳糖为原料,经过乙酰化、去乙酰化、硫苷化、异亚丙基化,苄基化得到目标化合物Ⅲ;在此基础上去异亚丙基化、碳酸酯化制得目标化合物Ⅰ。结果经同一条反应路线,高效地合成了两种3,4-位环状保护基保护的半乳糖乙硫苷供体,方法操作简单、环境友好、易于实施。其中,化合物Ⅰ为未经报道的新化合物,其结构经1HNMR、13 CNMR及HR-MS确证。结论文中结果为后续研究1,2-顺式半乳糖苷键的立体选择性合成奠定了基础。OBJECTIVE To investigate a practical and convenient method to synthesize 3,4-penta cyclic-protected thio-galactoglycoside donors.METHODS The target compound was synthesized from D-galactose via acetylation,deacetylation,thiolation,isopropylation,benzylation to get compoundⅢ,and then deisopropylation,carbonation to get compoundⅠ.RESULTS Two kinds of 3,4-penta cyclic-protected thio-galactoglycoside donors were synthesized efficiently via the same reaction route.The compoundⅠhas not been reported to date.The chemical structure of this compound was confirmed by 1HNMR,13CNMR and HR-MS spectra.CONCLUSION The study has laid a foundation of stereoselective synthesis of 1,2-cis galactoglycoside.

关 键 词：糖化学 1 2-顺式半乳糖 供体 设计 合成 工艺优化 保护基 核磁共振波谱 

分 类 号：R914[医药卫生—药物化学]