Facile transformation of β-D-ribofuranosyl purines and pyrimidines into their respective 3′-deoxy-threo-pentofuranosyl nucleosides

Abstract

Practical syntheses of 3′-deoxy-β-D-threo-pentofuranosyl-uracil, -cytosine, -adenine, and -guanine (3U, C, A, G) from the corresponding ribonucleosides by two one-pot reactions with readily accessible reagents are described. The key reactions are the selective 3′-O-methanesulphonylations of the ribonucleosides, the deoxygenative [1,2]-hydride shift of the methanesulphonates, and the reduction of in situ generated 3′-deoxy-2′-keto nucleosides therefrom.