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Synthesis of 9-[2-O-(2-Methoxyethyl)-β-D-Ribofuranosyl]purines Using 1- Methanesulfonyloxy-2-Methoxyethane

[ Vol. 2 , Issue. 4 ]

Author(s):

Grigorii G. Sivets, Jouko Vepsalainen and Igor A. Mikhailopulo   Pages 343 - 348 ( 6 )

Abstract:


1-Methanesulfonyloxy-2-methoxyethane (1; MsO-MOE) was used for alkylation of adenosine and 2-aminoadenosine. 2-O-MOE derivatives of adenosine (3), 2-aminoadenosine (7) and guanosine (10) have been prepared in 47, 44 and 81% isolated yields, respectively. The stereochemistry of the pentofuranose rings of the isomeric 2-O-MOE and 3-O-MOE purine nucleosides is very similar and, moreover, alkylation of either 2- or 3-hydroxyls has practically no effect upon the stereochemistry of the parent nucleosides.

Keywords:

nucleosides, purine, o-moe derivatives, methanesulfonyloxy-methoxyethane, stereochemistry

Affiliation:

University of Kuopio, Department of Pharmaceutical Chemistry, P.O. Box 1627, FIN-70211 Kuopio, Finland.



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