4-烯-6-氧代-3β-硫酸酯钠甾体化合物的合成研究  

Synthesis of Sodium 4-ene-3β-hydroxy-6-oxy-steroids Sulfated

作　　者：王辉[1] 李莹[1] 崔建国[1] 

机构地区：[1]广西师范学院化学系,广西南宁530001

出　　处：《广西师范学院学报（自然科学版）》2008年第3期63-67,共5页Journal of Guangxi Teachers Education University(Natural Science Edition)

基　　金：国家自然科学基金(20562001);广西科学基金(桂科基057554)资助

摘　　要：该文对天然存在的甾醇化合物1a-c进行结构改造,经过PCC氧化得到4-烯-3,6-二羰基甾体化合物2a-c,然后在钴离子存在的条件下用硼氢化钠选择性还原2a-c,得到4-烯-3-羟基-6-酮甾体化合物3a-c,3a-c利用三乙胺-三氧化硫复合物进行硫酸酯化,得到产物4a-c.然后4a-c通过阳离子(钠型)交换树脂进行Na+交换得到目标产物4-烯-6-氧代-3β-硫酸酯钠盐5a-c.5a-c是未见报道的新化合物.In recent years, the sodium polyhydroxysterols sulfated greatly attract the attention of organic chemists and biomedical scientists due to their novel structures and biological activities against cancer and micropathogens. Using natural sterols （la-c） as starting materials, sodium 4-ene-3β-hydroxy-6-oxysteroids sulfated （5a-c） was synthesized in 4 steps with a high overall yield. First, la-c were transformed into the corresponding 4-ene-3, 6-dione-steroids （2a-c） via oxidation with pyridinium chlorochromate （PCC）. The reduction of 2a-c by NaBH4 in the presence of CoCl2 gave 4-ene-3β-hydroxy-6-oxy-steroids （3a-c）. The reaction of 3a-c with triethylamine-sulfur trioxide complex offered the ammonium 4-ene-3β- hydroxy-6-oxy-steroids sulfated （4a-c） and the treatment of 4a-c by Cation exchange resin 732 （sodium form） gave the target steroid 5a-c.

关 键 词：甾醇 4-烯-6-氧代-3β硫酸酯钠盐 合成 

分 类 号：O629.29[理学—有机化学]