Mitsunobu coupling of nucleobases and alcohols: an efficient, practical synthesis for novel nonsugar carbon nucleosides

…, S Sengupta, JL Petersen, NG Akhmedov…

Index: Lu, Weibing; Sengupta, Sujata; Petersen, Jeffrey L.; Akhmedov, Novruz G.; Shi, Xiaodong Journal of Organic Chemistry, 2007 , vol. 72, # 13 p. 5012 - 5015

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Citation Number: 43

Abstract

A simple facile synthesis of substituted purine derivatives has been developed by using Mitsunobu conditions for an alcohol and a respective nucleobase. A wide range of alcohols produces good to excellent yield (> 90%). The resulting purine analogues show good regioselectivity with N-9 substitution as the dominant products in most of the cases. Application of diastereospecific alcohols reveals a complete inversion of the carbon ...

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