由2-脱氧-1-硫代糖苷合成芳基-2-脱氧-D-来苏糖型/阿洛糖型己吡喃糖苷
Synthesis of aryl-2-deoxy-D-lyxo/arabino-hexopyranosides from 2-deoxy-1-thioglycosides.
作者信息
Paul Somak, Jayaraman Narayanaswamy
机构信息
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.
出版信息
Carbohydr Res. 2007 Jul 23;342(10):1305-14. doi: 10.1016/j.carres.2007.02.030. Epub 2007 Mar 1.
The synthesis of either anomers of aryl 2-deoxy-D-glycopyranosides from 2-deoxy-1-thioglycosides is reported. The alpha-anomers form as the major product when thioglycosides react with differently substituted phenols and naphthols, in the presence of N-iodosuccinimide/triflic acid. On the other hand, reaction of the thioglycosides with bromine initially, followed by reaction with aryloxy anions lead to aryl 2-deoxy-beta-D-glycosides with high specificities.
报道了由2-脱氧-1-硫代糖苷合成芳基2-脱氧-D-吡喃葡萄糖苷的两种异头物。当硫代糖苷在N-碘代琥珀酰亚胺/三氟甲磺酸存在下与不同取代的酚和萘酚反应时，α-异头物作为主要产物形成。另一方面，硫代糖苷先与溴反应，然后与芳氧基阴离子反应，可高特异性地生成芳基2-脱氧-β-D-糖苷。
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