ChemInform Abstract: N‐HYDROPHOSPHORYL DERIVATIVES OF N‐ALKYLAMINOACETIC ACID IN THE SYNTHESIS OF 1,4,2‐DIAZAPHOSPHORINAN‐5‐ONES

Gololobov, Yu. G.; Nesterova, L. I.

doi:10.1002/chin.198320259

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“…Gololobov and Nesterova synthesized cyclic phosphonodipeptides via the annulation of N -benzylidenemethylamine and alkyl N -(dialkoxyphosphanyl)- N -alkylglycinates, which were prepared from alkyl N -(dichlorophosphanyl)- N -alkylglycinates with alcohols R 2 OH. The annulation was a sequence of P-nucleophilic addition and intramolecular aminolysis accompanying an N-nucleophilic addition followed by intramolecular aminolysis to yield imidazolidin-4-ones as byproducts ( Scheme 30 ) [ 61 ].…”

Section: Synthesis By Nucleophilic Additionmentioning

confidence: 99%

Synthetic Methods of Phosphonopeptides

2020

Molecules

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Phosphonopeptides are phosphorus analogues of peptides and have been widely applied as enzyme inhibitors and antigens to induce catalytic antibodies. Phosphonopeptides generally contain one aminoalkylphosphonic acid residue and include phosphonopeptides with C-terminal aminoalkylphosphonic acids and phosphonopeptides with a phosphonamidate bond. The phosphonamidate bond in the phosphonopeptides is generally formed via phosphonylation with phosphonochloridates, condensation with coupling reagents and enzymes, and phosphinylation followed by oxidation. Pseudo four-component condensation reaction of amides, aldehydes, alkyl dichlorophosphites, and amino/peptide esters is an alternative, convergent, and efficient strategy for synthesis of phosphonopeptides through simultaneous construction of aminoalkylphosphonic acids and formation of the phosphonamidate bond. This review focuses on the synthetic methods of phosphonopeptides containing a phosphonamidate bond.

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Section: Synthesis By Nucleophilic Additionmentioning

confidence: 99%

Synthetic Methods of Phosphonopeptides

2020

Molecules

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ChemInform Abstract: N‐HYDROPHOSPHORYL DERIVATIVES OF N‐ALKYLAMINOACETIC ACID IN THE SYNTHESIS OF 1,4,2‐DIAZAPHOSPHORINAN‐5‐ONES

Abstract: Läßt man auf das Dichlor‐amino‐phosphit (I) Wasser und Alkohole (II) einwirken, dann entstehen die unbeständigen sauren Phosphite (III).

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Synthetic Methods of Phosphonopeptides

Synthetic Methods of Phosphonopeptides

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