Preparation of trisodium O-monoalkyl and O-monoaryl diphosphates

Trisodium O-methyl, O-butyl, O-phenyl, and O-(4-nitrophenyl) diphosphates were synthesized from sodium dimethylamido-O-(2-cyanoethyl) phosphate and O-alkyl-and O-aryl phosphoric acids. While in the previously described method, sodium hydroxide was used for the preparation of O-phenyl diphosphate, in our current work, we present an improved protocol, where sodium methoxide is used to increase the yields of O-alkyl and O-aryl diphosphates. The structures of final compounds were determined by 1H NMR, 31P NMR, and IR spectroscopy. The sodium O-alkyl- and O-aryl diphosphate salts prepared by this method may be used for the study of biological activity of diphosphate analogues.

[1]  R. Billington,et al.  PPADS is a reversible competitive antagonist of the NAADP receptor. , 2007, Cell calcium.

[2]  H. Sigel,et al.  Acid-base and metal-ion-binding properties of 9-[2-(2-phosphonoethoxy)ethyl]adenine (PEEA), a relative of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). An exercise on the quantification of isomeric complex equilibria in solution. , 2005, Inorganic chemistry.

[3]  Erik De Clercq,et al.  Antiviral drugs in current clinical use. , 2004 .

[4]  C. Wagner,et al.  Pronucleotides: Toward the in vivo delivery of antiviral and anticancer nucleotides , 2000, Medicinal research reviews.

[5]  V. Kettmann,et al.  Model compounds in elucidating the structural basis of HIV retrovirus activity. Synthesis of trisodium O-monoalkyl- and O-monoaryldiphosphates. , 1996, Bollettino chimico farmaceutico.

[6]  V. Kettmann,et al.  MODEL COMPOUNDS IN ELUCIDATING THE STRUCTURAL BASIS OF HIV RETROVIRUSES ACTIVITY. A SIMPLE AND EFFECTIVE SYNTHESIS OF ETHOXYMETHYLPHOSPHONIC AND ACETO NYLPHOSPHONIC ACIDS , 1994 .

[7]  E. De Clercq,et al.  Intracellular delivery of bioactive AZT nucleotides by aryl phosphate derivatives of AZT. , 1993, Journal of medicinal chemistry.

[8]  T. Modro,et al.  AN IMPROVED SYNTHESIS OF MONOESTERS OF PHOSPHORIC ACID , 1992 .

[9]  E. Clercq,et al.  Phosphonylmethyl Ethers of Nucleosides and Their Acyclic Analogues , 1991 .

[10]  A. Holý,et al.  Synthesis of N-(2-phosphonylmethoxyethyl) derivatives of heterocyclic bases , 1989 .

[11]  E. De Clercq,et al.  Phosphonylmethoxyethyl purine derivatives, a new class of anti-human immunodeficiency virus agents , 1988, Antimicrobial Agents and Chemotherapy.

[12]  J. Balzarini,et al.  A novel selective broad-spectrum anti-DNA virus agent , 1986, Nature.

[13]  D. Graham,et al.  Phosphoric amides. 3. Acidic cleavage of the phosphorus-nitrogen bond in acyclic and cyclic phosphoramidates , 1981 .

[14]  N. Thuong,et al.  ACTION OF PROPARGYLIC ALCOHOL ON SEVERAL TRISUBSTITUTED PHOSPHITES , 1978 .

[15]  G. del Campo,et al.  Hydrolysis of synthetic pyrophosphoric esters by an isoenzyme of apyrase from Solanum tuberosum. , 1977, The Biochemical journal.

[16]  R. Naylor,et al.  Evidence for SN2(P) mechanism in the phosphorylation of alkaline phosphatase by substrates , 1971 .

[17]  P. Waldrep,et al.  The Structure of Couper's Compound. Chemical Studies and P31 Nuclear Magnetic Resonance Spectra on Couper's Compound and Related Structures1 , 1966 .

[18]  F. Lynen,et al.  Dinucleotidsynthesen mit Pyrophosphoryltetrachlorid. Eine Synthese von Coenzym A , 1962 .

[19]  F. Cramer,et al.  Zur Chemie der energiereichen Phosphate, X: Die Darstellung von Triestern der Pyrophosphorsäure und ihre Verwendung zur Synthese von Nucleotid-Derivaten , 1961 .

[20]  G. Tener 2-Cyanoethyl Phosphate and its Use in the Synthesis of Phosphate Esters1 , 1961 .

[21]  A. Martell,et al.  THE CARBOXYMETHYLATION OF AMINES. II. TRIGLYCINE , 1950 .

[22]  B. Axelrod Citrus fruit phosphatase. , 1947, The Journal of biological chemistry.