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

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.