Synthesis of new organophosphorus‐substituted mono‐ and bis(trimethylsilyl)amines with PCH<sub>2</sub>N fragments and their derivatives

Prishchenko, A. A.; Ливанцов, М. В.; Novikova, O. P.; Livantsova, L. I.; Petrosyan, V. S.

doi:10.1002/hc.20580

Cited by 46 publications

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“…In the course of studies on the reactivity of trimethylsilylated compounds, including (Me 3 SiO) 2 P-H ( 20 ), Prishchenko et al discovered several reaction variants that led to phosphinic compounds [ 53 , 54 , 55 ]. Among others, N -(methoxymethyl)bis(trimethylsilyl)amine ( 19 ) reacted with bis(trimethylsilyl) phosphonite in the presence of ZnCl 2 to yield the GlyPH analogue 21 , which was subsequently added to trimethylsilyl acrylate ( 22 ) [ 53 ]. Free Glyψ[P(O)(OH)CH 2 ]-Gly ( 23 ) was obtained after methanolysis with a total yield of 44% ( Scheme 5 ).…”

Section: Synthesis Of the Phosphinic αα'-Dipeptide Backbonementioning

confidence: 99%

Synthesis and Modifications of Phosphinic Dipeptide Analogues

Mucha

2012

Molecules

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Pseudopeptides containing the phosphinate moiety (-P(O)(OH)CH2-) have been studied extensively, mainly as transition state analogue inhibitors of metalloproteases. The key synthetic aspect of their chemistry is construction of phosphinic dipeptide derivatives bearing appropriate side-chain substituents. Typically, this synthesis involves a multistep preparation of two individual building blocks, which are combined in the final step. As this methodology does not allow simple variation of the side-chain structure, many efforts have been dedicated to the development of alternative approaches. Recent achievements in this field are summarized in this review. Improved methods for the formation of the phosphinic peptide backbone, including stereoselective and multicomponent reactions, are presented. Parallel modifications leading to the structurally diversified substituents are also described. Finally, selected examples of the biomedical applications of the title compounds are given.

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Section: Synthesis Of the Phosphinic αα'-Dipeptide Backbonementioning

confidence: 99%

Synthesis and Modifications of Phosphinic Dipeptide Analogues

Mucha

2012

Molecules

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ChemInform Abstract: Synthesis of New Organophosphorus‐Substituted Mono‐ and Bis(trimethylsilyl)amines with PCH₂N Fragments and Their Derivatives.

et al. 2010

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Synthesis and functionalization of organophosphorus‐substituted amines with PCH₂NH fragments

Prishchenko

Ливанцов

Livantsova

et al. 2010

Heteroatom Chemistry

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Synthesis of new organophosphorus‐substituted mono‐ and bis(trimethylsilyl)amines with PCH₂N fragments and their derivatives

Cited by 46 publications

References 10 publications

Synthesis and Modifications of Phosphinic Dipeptide Analogues

Synthesis and Modifications of Phosphinic Dipeptide Analogues

ChemInform Abstract: Synthesis of New Organophosphorus‐Substituted Mono‐ and Bis(trimethylsilyl)amines with PCH₂N Fragments and Their Derivatives.

Synthesis and functionalization of organophosphorus‐substituted amines with PCH₂NH fragments

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Synthesis of new organophosphorus‐substituted mono‐ and bis(trimethylsilyl)amines with PCH2N fragments and their derivatives

Cited by 46 publications

References 10 publications

Synthesis and Modifications of Phosphinic Dipeptide Analogues

Synthesis and Modifications of Phosphinic Dipeptide Analogues

ChemInform Abstract: Synthesis of New Organophosphorus‐Substituted Mono‐ and Bis(trimethylsilyl)amines with PCH2N Fragments and Their Derivatives.

Synthesis and functionalization of organophosphorus‐substituted amines with PCH2NH fragments

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Synthesis of new organophosphorus‐substituted mono‐ and bis(trimethylsilyl)amines with PCH₂N fragments and their derivatives

ChemInform Abstract: Synthesis of New Organophosphorus‐Substituted Mono‐ and Bis(trimethylsilyl)amines with PCH₂N Fragments and Their Derivatives.

Synthesis and functionalization of organophosphorus‐substituted amines with PCH₂NH fragments