The Synthesis of Hypodiphosphoric Acid and Derivatives with P-P Bond, including Esters and Diphosphine Dioxides: A Review

Abstract

The synthesis of hypodiphosphoric acid and its related compounds began in 1877, but no summary of the synthetic efforts has been reported. This review includes published papers related to the molecules containing the >P(=O)-P(=O)< fragment, which notably resembles the structure of the >P(=O)-O-P(=O)< moiety, the essential building block of many important molecules found in nature and in the field of medicinal chemistry. This review covers the strategies related to the synthesis of hypodiphosphoric acid (former name hypophosphoric acid), its ester form, and diphosphine dioxides. Finally, some properties and applications of these structures studied during this period are presented.

Synthesis and Spectroscopic Characterization of Selected Phenothiazines and Phenazines Rationalized Based on DFT Calculation

“…Inspired by the work of Prof. Keglevich’s team, we performed a similar type of reaction; however, as a phosphorylating agent, we chose 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide. This electrophile is known for its high tendency to crystallize ( Scheme 2 ) [ 28 , 29 ]. In order to synthesize the 5,5-dimethyl-2-(10 H -phenothiazin-10-yl)-1,3,2-dioxaphosphinane 2-oxide ( 2a ), we performed a reaction between the in situ generated sodium salt of phenothiazine and 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide in THF.…”

Dimethylphosphite electrosynthesis from inorganic phosphorus building blocks via oxidative coupling

“…A possible chemical explanation of this is that the positive current entails the 1 e − oxidation of H 3 PO 2 to [˙PH 2 O 2 ] + via cleavage of the weak P–H bond. 15,24 This radical species can then presumably further react with other species in the electrolyte ( e.g. CH 3 OH) or dimerize with proximal H 3 PO 2 species to form pyrophosphate-like products, the latter of which we tentatively attribute to the site-blocking inactive species.…”

Substrate Specificity of T7 RNA Polymerase toward Hypophosphoric Analogues of ATP

“…Hypodiphosphoric acid has been considered to interact with placental alkaline phosphatase (PLAP) 41 and tissue-nonspecific alkaline phosphatase (TNAP) 42 and was demonstrated to be a substrate of pyrophosphorolysis catalyzed by HIV-1 reverse transcriptase; 43 however, to date, little is known about the other biological properties of this molecule. 44 Thus, the obtained results make a significant contribution toward the knowledge about this molecule and the potential activity of its derivatives.…”

“…Whereas a slight decrease of the in vitro transcription activity with a higher concentration of pyrophosphoric acid has been previously reported, and this was observed in our studies (Figure S23), the inhibitory activity of hypodiphosphoric acid toward T7 RNA polymerase has never been demonstrated. Hypodiphosphoric acid has been considered to interact with placental alkaline phosphatase (PLAP) and tissue-nonspecific alkaline phosphatase (TNAP) and was demonstrated to be a substrate of pyrophosphorolysis catalyzed by HIV-1 reverse transcriptase; however, to date, little is known about the other biological properties of this molecule . Thus, the obtained results make a significant contribution toward the knowledge about this molecule and the potential activity of its derivatives.…”