PHOSPHONATES - A NOVEL TYPE NUCLEOTIDE ANALOGS RELATED TO HPMPA. I. DERIVATIVES WITH L-arabino, D-arabino, 2-DEOXY-L-erythro AND 2-DEOXY-L-threo CONFIGURATION

Article abstract of DOI:10.1135/cccc19932159

<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 Michaelis-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 derovatives react with sodium salt of adenine to give N⁹-substituted products which after total deprotection afford the title 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.