Phosphonic acid esters synthesis

Burkhouse, D. and Zimmer, H., Novel synthesis of 1-alkoxy-l-arylmethane-phosphonic acid esters, Synthesis, 330, 1984. 

Makosza, M. and Wojciehowski, K., Synthesis of phosphonic acid esters in a solid-liquid catalytic two-phase system, Bull. Pol. Acad. Sci. Chem., 32, 175, 1984. 

Bis(hydroxymethyl)phosphonic acid esters that incorporated thymine were employed as a backbone to prepare short oligonucleotide chains. This chain was prepared by condensation of the bis(4,4 -dimethoxytrityl) protected phosphonic acid and iV or N -(2-hydroxyethyl)thymine in the presence of l-(2-mesitylenesul-fonyl)-3-nitro-l,2,4-triazole or by an Appel reaction with or N -(2-aminoethyl)thymine (89a-h). Selective removal of one DMT-group and phos-phitylation yielded the building blocks for solid supported synthesis of the short oligomers by the phosphoramidite approach. Holy has reported the synthesis of 8-amino and 8-substituted amino derivatives of acyclic purine nucleotide analogues. The 8-amino, 8-methylamino- and 8-dimethylamino-adenine and -guanine analogues of iV-(2-phosphonomethoxyethyl) and (S)-iV-(3-hydroxy-2-phosphono-methoxy-propyl) derivatives of purines (90a-i), were prepared by... 

Gross, H., and Seibt, H., a-Substituted phosphonic acid esters. Part 10. Synthesis of chloro(methoxy )meth-ylphosphonic esters and chloro(methylthio)methylphosphonic esters, J. Prakt. Chem., 312, 475, 1970. 

Obrycki. R.. and Griffin. C.E.. Phosphonic acids esters. Part 19. Syntheses of substimted phenyl- and arylphosphonates by the photoinitiated arylation of trialkyl phosphites, J. Org. Chem., 33, 632, 1968. Engel. R.. Synthesis of Carbon-Phosphorus Bonds, CRC Press, Boca Raton, 1988, p. 137. 

Heep, U., On the synthesis of heterocyclic phosphonic acid esters, Justus Liebigs Ann. Chem., 578, 1973. 

Bakalarz-Jezioma, A., Helinski, J., and Krawiecka, B., Synthesis of multifunctionahzed phosphonic acid esters via opening of oxiranes and azetidinium salts with phosphoryl-substituted carbanions,... 

Many communications have concentrated on specific amino phosphonic acids or derivative types. Thus, esters of phosphonoaminoacetic add were obtained by the reactions between trialkyl (ethyl) phosphite and (218) and which are thought to proceed via the phosphorane (219). A sequence has been presented for the preparation of the mono- and di-benzyl esters of N-chz protected (a-aminoben-zyl)phosphonic acid. A synthesis of (aminomethylene)bisphosphonic acid from dibenzylamine, dibenzyl hydrogenphosphonate and triethyl orthoformate has been noted and the asymmetric hydrogenation of (220) in the presence of chiral phosphine catalysts yields samples of (221) with e.e.s of 63-96%. The pyrrolidine-based compound (222) has been prepared from methyl S)-N-methoxycarbonyl-4-oxo-2-pyrrolidinecarboxylate and iV-coupled 4-amino-butanal diethyl acetals were the starting materials in syntheses of the pyrrolidine-2-phosphonic add derivatives (223) in which Z represents the iV-protected amino add or peptide moiety. ... 

There have been further applications of MesSil and MesSiBr as dealkylating agents for ethers, esters, phosphonic acid esters, and alcohols, the last reaction using McsSil being a useful alkyl iodide synthesis. MesSil also converts acetals into ketones or sulphoxides into sulphides, whilst a mixture of PhSiMes and I2 is capable of dealkylating esters at ca. 110°C. ... 

The synthesis of F-labeled stilbenes [ F]2g, [ F]3g, and [ F]4e ( -isomers) by the FIorner-Wadsworth-Emmons reaction was accomplished [83]. This carbonyl-olefination reaction was performed via a multistep/one-pot reaction by the coupling of benzylic phosphonic acid esters (3,5-bis-methoxymethoxybenzyl)-phosphonic acid diethyl ester, (4-methoxymethoxybenzyl)phosphonic acid diethyl ester, and (4-dimethylaminobenzyl)phosphonic add diethyl ester with 4-[ F]fluor-obenzaldehyde. The radiochemical yields ranged from 9 to 22%. Three new polyfluorinated compounds ([( )-4-(4-bromostyryl)-2,3,5,6-tetrafluorobenzonitrile]x-[( )-4-(4-bromo-2,3,5,6-tetrafluorostyryl)benzonitrile]i K) were obtained by the Homer-Wadsworth-Emmons approach to study intermolecular interactions in the crystal state and the formation of cocrystals [84]. 

Sodium hydride Homer synthesis Ethylene derivs. from 0X0 compds. and phosphonic acid esters... 

Diethyl methylphosphonate allowed to react at -70 to -60° with n-butyllithium in tetrahydrofuran, then with Cul at -35°, finally with acetyl chloride product. Y 95%. F. e., also with CuBr, and synthesis of / -ketothionophosphonic acid esters, s. P. Savignac and F. Mathey, Tetrah. Let. 1976, 2829 1-alkylated y -keto-phosphonic acid esters s. Synthesis 1976, 166,... 

Synthesis of ethylene derivatives from 0x0 compounds and phosphonic acid esters or phosphine oxides... 

Chiral cyclic esters of phosphonic acid in the synthesis of coordination compounds and homogeneous asymmetric catalysis 99KK83. 

Scheme (17) illustrates the synthesis of the diphenyl ester (118) of (l-amino-2-propenyl)phosphonic acid (119), an... 

Esters of [1-(diethoxyphosphinyloxy)perfluoro-l-alkene]-phosphonic acid appear to be effective reagents for the synthesis of perfluoro-a,B-unsaturated carboxylic acids and their derivatives presumably an initially-generated perfluoroketene (166 ) is acted upon by a nucleophile (NuH=RNH2, I NH, or ROH). The ( E) / (Z) ratio of the product components increases with increasing length of R. 2 ... 

Mashida and Sato [40] developed a method for the synthesis of the target compounds, based on the intramolecular rearrangement of the butyl esters of 3-hydrox-ipropene-l-phosphonic acid (Scheme 9). 

Several methods for the preparation of the parent compound in this system, tris(trimethylsilyl)phosphite, have been reported.114 118 The application of this and related reagents in reaction with alkyl halides has been reported and used for the preparation of a variety of phosphonic acid analogues of phospholipids.114119-124 Interestingly, alkyl chlorides appear to be more reactive with the silyl reagents than do alkyl iodides, a reversal of the normally observed trend with alkyl esters of the phosphorus acids. (The particular use of silyl phosphorus reagents for the synthesis of biologically significant compounds has... 

Issleib, K., Dopfer, K.-P, and Balszuweit, A., Contribution to the synthesis of a-aminoalkane phosphonic acid dialkyl esters, Z. Anorg. Allg. Chem., 444,249, 1978. 

ASYMMETRIC SYNTHESIS OF DIETHYL (R)-(-)-(1-AMINO-3-METHYLBUTYL)PHOSPHONATE (Phosphonic acid, (l-amino-3-methylbutyl)-, diethyl ester, (R)-)... 

Fields EK (1952) The synthesis of esters of substituted amino phosphonic acids. J Am Chem Soc 74(6) 1528-1531... 

Pudovik AN (1952) Addition of dialkyl phosphites to imines. New method of synthesis of esters of amino phosphonic acids. Dokl Akad Nauk SSSR 83 865-868... 

The Synthesis of (S)-[l-(Acetoxyl)-4-(3-Phenyl)Butyl]Phosphonic Acid Diethyl Ester (Anticholesterol Drug)... 

S)-[l-(acetoxyl)-4-(3-phenyl)butyl]phosphonic acid diethyl ester (10) is a key intermediate required for the synthesis of (11) (Scheme 7.6), which is being... 

For the synthesis of peptides, the phosphonic moiety in most cases should be masked as a diester. Diesters of 1-aminoalkylphosphonic acids can be synthesized directly or by esterification of 1-aminoalkylphosphonic acids. If peptides with the free phosphonic moiety are the desired products, then methods are available for the selective removal of both ester groups. Peptides with a free C-terminal phosphonic acid functionality can be synthesized directly from the free 1-aminoalkylphosphonic acids. In addition, methods for synthesis of the peptides with C-terminal phosphonates directly from the peptides are also available. In general, most methods for the synthesis of peptide bonds work well for the synthesis of peptides with C-terminal phosphonates if diesters of 1-aminoalkylphosphonic acids are used. Bulky diaryl esters give yields similar to the diethyl esters. Therefore, the most challenging step in the synthesis of peptide phosphonates is the synthesis of 1-aminoalkylphosphonic acids and/or their esters. It is not possible in this section to review all of the literature data and only examples of several general methods are included. This will still provide a variety of methods for the efficient synthesis 1-aminoalkylphosphonic acids, their esters, and related peptide derivatives. 

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