Synthesis of C2-β-Fluoro-Substituted Adenine Nucleosides Via Pivaloyl Derivatives of Adenosine and 3 -Deoxyadenosine

Title: Synthesis of C2-β-Fluoro-Substituted Adenine Nucleosides Via Pivaloyl Derivatives of Adenosine and 3 -Deoxyadenosine

Volume: 3 Issue: 5

Author(s): Grigorii G. Sivets, Elena N. Kalinichenko and Igor A. Mikhailopulo

Affiliation:

Keywords: Nucleosides, purine, 2'-deoxyfluoro derivatives, PSEUROT analysis

Abstract: Syntheses of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (9) its 3-deoxy derivative, 9-(2,3- dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (16), with the DAST treatment of the corresponding 3,5- di-O-pivaloyladenosine (7) and its 3-deoxy derivative 14 are described. The role of the pentofuranose ring stereochemistry of nucleosides 7 and 14 in the DAST fluorination is discussed. Stereochemistry of compounds 7 and 14 as well as fluorides 9 and 16 was studied by the PSEUROT 6.3 program.

Cite this article as:

Sivets G. Grigorii, Kalinichenko N. Elena and Mikhailopulo A. Igor, Synthesis of C2-β-Fluoro-Substituted Adenine Nucleosides Via Pivaloyl Derivatives of Adenosine and 3 -Deoxyadenosine, Letters in Organic Chemistry 2006; 3 (5) . https://dx.doi.org/10.2174/157017806776611953