脑靶向脂质体配体葡萄糖-胆甾偶联物的设计与合成

Design and synthesis of glucose-cholesterol as ligand for brain targeting liposomes

目的合成具有酯水两性的脑靶向脂质体配体葡萄糖-胆固醇偶联物。方法将胆固醇3位羟基与对甲苯磺酰氯成酯后,与乙二醇取代,并氧化制得2-(5-胆甾烯-3-β-氧基)-1-乙酸,再与1,2,3,4-四-O-三甲硅基-β-D-吡喃葡萄糖在缩合剂DCC的作用下成酯,由三氟乙酸四氢呋喃溶液脱保护后得到目标配体。结果合成了1个葡萄糖胆甾偶联物。结论目标化合物以及重要中间体均经IR、1HNMR、MS等确证。

OBJECTIVE To synthesize an amphiphilic glucose-cholesterol as ligand for brain targeting liposome.METHODS The synthesis of title compound started from cholesterol by tosylation,substitution and oxidation to afford acid 3.The compound 3 was coupled with 1,2,3,4-tetra-O-trimethylsilyl-β-D-glucopyranose in the presence of DCC to get compound 4.Compound 4 was deprotected in tetrahydrofuran with TFA to obtain the title compound L.RESULTS The title compound was successfully synthesized.CONCLUSION The chemical structure of the target compound and intermediate were characterized by IR,1HNMR and MS respectively.