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

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

Volume: 2 Issue: 4

Author(s): Grigorii G. Sivets, Jouko Vepsalainen and Igor A. Mikhailopulo

Affiliation:

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

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.

Cite this article as:

Sivets G. Grigorii, Vepsalainen Jouko and Mikhailopulo A. Igor, Synthesis of 9-[2-O-(2-Methoxyethyl)-β-D-Ribofuranosyl]purines Using 1- Methanesulfonyloxy-2-Methoxyethane, Letters in Organic Chemistry 2005; 2 (4) . https://dx.doi.org/10.2174/1570178054038948