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

Nucleosides, nucleotides & nucleic acids (2003-05-15)
Shigetada Kozai, Tomoyo Fuzikawa, Keisuke Harumoto, Tokumi Maruyama
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.

MATERIALS
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Brand
Product Description

Sigma-Aldrich
2,3,4-Trimethoxybenzyl alcohol, 97%