1β-/3R-芳基硫代糖的区域与立体选择性合成

Regio-and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar

硫代糖因具有优良的生物活性在生物医药领域备受关注,化学合成是得到硫代糖的重要途径.采用6-膦酸酯3,4-碳酸酯半乳烯糖和硫酚为原料,分别以Pd_(2)(dba)_(3)和NiBr_(2)为催化剂调控了1β-芳基硫代糖和(3R)-芳基硫代糖的区域和立体选择性合成.目标化合物的结构通过核磁共振、高分辨质谱和单晶X射线衍射进行了表征.该合成方法对各类官能团取代的硫酚都有良好的兼容性,可用于活性天然产物的硫糖基化修饰,为1β-/(3R)-芳基硫代糖化合物库的快速构建和药物发现提供了新方法.

Thiosugars have attracted much attention in the field of pharmaceuticals because of their excellent biological activities,and chemical synthesis is an important way to obtain thiosugars.Using 6-O-diphenylphosphoryl-3,4-O-carbonate-D-galactal and thiophenols as starting materials,the regio-and stereo-selective syntheses of 1β-/(3R)-aryl thiosugars were controlled with NiBr_(2) and Pd_(2)(dba)_(3) catalysts,respectively.The structures of the target compounds were characterized by nuclear magnetic resonance,high-resolution mass spectrometry and single crystal X-ray diffraction.This method exhibited favourable compatibility with various functional groups substituted thiophenols,which could be used for the structural modification of active natural products.The research work is help for the rapid construction of the compound library of 1β-/(3R)-aryl thiosugars for drug discovery.