Phosphonate analogues of nucleoside polyphosphates

Abstract

This article provides an overview of the efforts toward the synthesis of nucleoside polyphosphate mimics featuring a P-CXY-P scaffold. The following synthetic approaches to these compounds are summarized: (i) nucleophilic displacement of 5´-O-tosyl nucleoside by the ammonium salts of methylenebisphosphonic acid; (ii) synthesis via activated phosphate/phosphonate substrates; (iii) Mitsunobu coupling between a nucleoside and methylenebisphosphonic acid; (iv) phosphorylation of a protected nucleoside under Yoshikawa's reaction conditions with methylenebis(phosphonic dichloride); (v) synthesis via nucleophilic cleavage of cyclic trimetaphosph(on)ates; (vi) enzyme-mediated reactions.

Chemistry of difluoromethylene phosphonates: history, state of the art, and prospects

“…However, the original Blackburn compounds, difluoromethylene bisphosphonates, have conceptually always been a separate class of compounds despite being a subclass of CF2-phosphonates in a strict chemical sense. Their chemistry has recently been reviewed in several publications by Romanenko and Kukhar and will not be discussed here [52][53][54]. In some cases, the closely related monofluoromethylene phosphonates have been proven superior to CF2-phosphonates, but chemical methods for their preparation, apart from fluorination, are usually specific to them [55].…”