Tetrahedron

Nucleophilic substitution approach to 4′-substituted thymidines by employing 4′-benzenesulfonyl leaving group

H Shimada, S Kikuchi, S Okuda, K Haraguchi…

Index: Shimada, Hisashi; Kikuchi, Satoshi; Okuda, Saori; Haraguchi, Kazuhiro; Tanaka, Hiromichi Tetrahedron, 2009 , vol. 65, # 31 p. 6008 - 6016

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Citation Number: 9

Abstract

Synthesis of 4′-substituted thymidines was investigated based on nucleophilic substitution using organosilicon and organoaluminum reagents. Two substrates having a benzenesulfonyl leaving group at the 4′-position were prepared for this purpose: 1-[4- benzenesulfonyl-3, 5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-α-l-threo-pentofuranosyl] thymine (8α) and the 4′-(benzenesulfonyl) thymidine derivative (8β). The reaction of 8α ...