Nucleosides, Nucleotides & Nucleic Acids 2003-02-01

A new method for the synthesis of 2'-O-benzyladenosine using Mitsunobu reaction.

Shigetada Kozai, Tomoyo Fuzikawa, Keisuke Harumoto, Tokumi Maruyama

Index: Nucleosides Nucleotides Nucleic Acids 22(2) , 145-51, (2003)

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Abstract

A new method to introduce a benzyl group onto the 2'-OH of purine ribonucleoside is described. Thus, 6-chloropurine 3'-O-benzoylriboside and its 5'-O-trityl congener were condensed with benzyl alcohol using the Mitsunobu reaction to give the 2'-O-benzyl derivative. The yields were varied from 4.6 to 62.9% depending on the solvent used. The product was converted to adenosine, indicating that the stereochemistry at C-2' is retained.