作者:Éva Bozó、Sándor Boros、János Kuszmann
DOI:10.1016/s0008-6215(97)00001-3
日期:1997.3
4-di-O-benzoyl-1,5-anhydro-5-thio- d -threo-pent-1-enitol, the hydrogen bromide addition products of which were treated with sodium 4-cyanobenzenethiolate to give the anomeric mixture of the corresponding thioglycosides in low yield with an α,β-ratio of 3:7. When the mixture of the hydrogen bromide addition products was converted with silver acetate into their 1- O -acetates and condensation with 4-cyanobenzenethiol
摘要在4-甲基吡啶存在下,用锌将2,3,4-三-O-乙酰基-5-硫代-α-d-吡喃吡喃糖基溴化物转化为3,4-二-O-乙酰基-1,5-脱水-5-硫代-d-苏-戊-1-烯醇5.用N-碘琥珀酰亚胺-水在乙腈中处理5,得到的混合物经硼氢化钠-氯化镍还原并随后乙酰化后,仅得到1,3, 4-三-O-乙酰基-2,5-脱水-5-硫代-d-木糖醇。将5脱乙酰化并随后进行苯甲酰化,得到3,4-二-O-苯甲酰基-1,5-脱水5-硫代d-苏式戊-1-烯醇,其溴化氢加成产物用4-钠处理氰基苯硫醇盐以低产率得到相应硫代糖苷的异头混合物,α,β比率为3:7。当将溴化氢加成产物的混合物用乙酸银转化为它们的1-O-乙酸酯并在三甲基甲硅烷基三氟甲磺酸酯的存在下与4-氰基苯硫醇缩合时,以α,β-比率高收率获得硫代糖苷。 15:85。该混合物脱乙酰基得到标题化合物,其在大鼠中显示出高的口服抗血栓形成活性。将2-脱氧-5-硫代-