Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad 500 007, India.
Carbohydr Res. 2012 May 1;352:191-6. doi: 10.1016/j.carres.2012.01.018. Epub 2012 Jan 28.
Syntheses of six N-homobicyclic dideoxynucleoside analogues are described. The reaction of mannose diacetonide with trimethylsulfoxonium iodide gave a mixture of diastereomeric hydroxymethyl mannose diacetonides in a ratio of 2:5, which was separated by fractional crystallization. The two stereoisomers were converted to bicyclic furanolactols each of which was coupled with three nucleoside bases. Further debenzylations gave the six target N-homobicyclic dideoxynucleosides.
描述了六种 N-同型双环脱氧核苷类似物的合成。在三甲基碘化亚砜的作用下，甘露糖二乙酸酯生成了 2:5 的非对映异构体混合物，通过分步结晶进行分离。两种立体异构体都转化为双环呋喃内酯醇，每个都与三个核苷碱基偶联。进一步脱苄基得到了六种目标 N-同型双环脱氧核苷。
