Modular and practical synthesis of 6-substituted pyridin-3-yl C-nucleosides

N Joubert, R Pohl, B Klepetarova…

Index: Joubert, Nicolas; Pohl, Radek; Klepetarova, Blanka; Hocek, Michal Journal of Organic Chemistry, 2007 , vol. 72, # 18 p. 6797 - 6805

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Citation Number: 65

Abstract

A novel modular and practical methodology for preparation of 6-substituted pyridin-3-yl C- nucleosides was developed. The Heck reaction of 2-chloro-5-iodopyridine with a 3'-TBDMS- protected glycal gave a 6-chloropyridin-3-yl nucleoside analogue, which was then desilylated, selectively reduced, and reprotected to give the TBDMS-protected 6- chloropyridin-3-yl C-2'-deoxyribonucleoside as a pure β-anomer in a total yield of 39% ...