【摘要】 目的研究恩曲他滨顺式和反式消旋体的合成新方法。方法以苯甲酰氧基乙醛和2,5-二羟基-1,4-二噻烷为起始原料,在对甲苯磺酸催化下环合,得1,3-氧硫杂环戊烷半缩醛(5),用SOC l2/DMF将半缩醛羟基氯代后,与硅烷化的N4-乙酰基-5-氟胞嘧啶(7)偶合,分离顺/反异构体后,用浓氨水/甲醇脱保护,分别得恩曲他滨顺式和反式消旋体。结果目标物的化学结构经1HNMR、13CNMR、MS和元素分析确证,总收率分别为51.1%和20.9%。结论方法与文献比较,具有反应条件温和、操作简便、收率高等优点。更多还原

【Abstract】 OBJECTIVE To synthesize cis and trans-(±)-isomer of Emtricitabine.METHODS cis and trans-(±)-isomer of Emtricitabine were synthesized from benzoyloxyacetaldehyde and 1,4-dithiane-2,5-diol.The key steps included chlorination of 1,3-oxathiolane lactol(5) by SOCl2/DMF,followed by coupling with silylated N4-acetyl-5-fluoro-cytosine and subjected to flash chromatography.The protected group was removed by NH4OH/MeOH at room temperature to produce the desired compounds.RESULTS The chemical structures of target compounds were determined by 1H NMR,13C NMR, MS and elemental analysis.The overall yield was 51.1 % for cis-(±) isomer and 20.9 % for trans-(±) isomer.CONCLUSION This method has the advantages of mild reaction condition,simple manipulation and high yield.更多还原