Collect. Czech. Chem. Commun. 1993, 58, 2159-2179
https://doi.org/10.1135/cccc19932159

[5-(Adenin-9-yl)-5-deoxypentofuranosyl]phosphonates - A Novel Type of Nucleotide Analogs Related to HPMPA. I. Derivatives with L-arabino, D-arabino, 2-Deoxy-L-erythro and 2-Deoxy-L-threo Configuration

Miroslav Otmar, Ivan Rosenberg, Milena Masojídková and Antonín Holý

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic

This article is part of serial [5-(Adenin-9-yl)-5-deoxy-L-pentofuranosyl]phosphonates - A Novel Type of Nucleotide Analogs Related to HPMPA.

Abstract

[5-(Adenin-9-yl)-5-deoxypentofuranosyl]phosphonates, a new type of nucleotide analogs with fixed HPMPA structure, have been prepared. The synthesis of compounds of L-arabino (IIa, IIb), D-arabino(XIVa, XIVb), 2-deoxy-L-erythro(IIIa, IIIb) and 2-deoxy-L-threo(IVa, IVb) configuration is based on the Michelis-Arbuzov reaction of the fully protected methyl glycosides with triethyl phosphite and trimethylsilyl triflate which leads to anomeric mixture of diethyl (L-pentofuranosyl) phosphonates. The protected 5-O-tosyl derivatives react with sodium salt of adenine to give N9-substituted products which after total deprotection afforded the tittle nucleotide analogs. The fixation of the partial structure of HPMPA to form five-membered ring leads to a significant decrease, or a total loss, of biological activity.