一个新的脂水两性的胆甾半乳糖苷的设计与合成  

Design and synthesis of amphiphilic thiogalactopyranoside

作　　者：范琴[1] 海俐[1] 吴勇[1] 

机构地区：[1]四川大学华西药学院,成都610041

出　　处：《四川大学学报（自然科学版）》2007年第2期403-406,共4页Journal of Sichuan University(Natural Science Edition)

基　　金：国家自然科学基金(30672537);教育部博士点基金(20050610085)

摘　　要：设计并合成了一个新的脂水两性胆甾半乳糖苷偶联物T,该化合物可用作脂质体配体,提高阳离子脂质体的肝靶向性.目标化合物T的合成方法如下:以胆甾烯对甲苯磺酸酯1为起始原料,与己二醇作用后得醇2,2经甲烷磺酰化、碘代制得碘代物4,4随后与2,3,4,6-四-O-乙酰基-1-巯基-β-D-吡喃半乳糖5成硫醚得到糖苷6,再经甲醇钠处理,脱去乙酰基制得目标物T,合成的目标化合物及中间体均经1HNMR、IR和MS确证结构.In order to improve the hepatocyte targeting capability of cationic liposomes, we have designed and synthesized a novel arnphiphilic cholesterylated thiogalactoside T, which can serve as the liposomes ligand. Starting from cholesteryl tosylate 1, the title compound has been prepared as follows, the initial reaction between 1 and hexanediol forming alcohol 2 is followed by mesylation and iodiation to give 4, intermediate 4 is then condensed with 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranose 5 to afford 6, which is subsequently deacetylated to give title compound T in the presence of sodium methoxide. The synthesized title compound and intermediates were characterized by 1^HNMR, IR and MS.

关 键 词：肝靶向 胆甾半乳糖苷衍生物 合成 

分 类 号：R914.5[医药卫生—药物化学]