Tetrahedron

Improved synthetic approaches toward 2′-O-methyl-adenosine and guanosine and their N-acyl derivatives

L Beigelman, P Haeberli, D Sweedler, A Karpeisky

Index: Beigelman, Leonid; Haeberli, Peter; Sweedler, David; Karpeisky, Alexander Tetrahedron, 2000 , vol. 56, # 8 p. 1047 - 1056

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Citation Number: 26

Abstract

We developed several improved approaches toward 2′-O-methyl adenosine and guanosine and their N-acyl derivatives.(a) Transglycosylation of N4-acetyl-5′, 3′-di-O- acetyl-2′-O-methyl cytidine with N6-Bz-adenine provided N6-benzoyl-5′ 3′-di-O-acetyl- 2′-O-methyl adenosine in 50% yield.(b) Regioselective methylation of 2-amino-6-chloro purine riboside with MeI/NaH followed by hydrolysis provided 2′-O-Me-guanosine in ...