A convenient catalytic silicon-assisted route towards new non-proteinogenic amino acids with methylenebisphosphonic acids moieties

被引：25

作者：

Prishchenko, Andrey A. ^{[1
]}

Alekseyev, Roman S. ^{[1
]}

Livantsov, Mikhail, V ^{[1
]}

Novikova, Olga P. ^{[1
]}

Livantsova, Ludmila, I ^{[1
]}

Petrosyan, Valery S. ^{[1
]}

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2021年 / 949卷

基金：

俄罗斯科学基金会;

关键词：

Tris(trimethylsilyl) phosphite; Non-proteinogenic amino acids; Trimethylsilyl triflate; Functionalized; aminomethylenebisphosphonic acids; Promising antiviral substances; KEY SYNTHON; DERIVATIVES; CHEMISTRY; MILD;

D O I：

10.1016/j.jorganchem.2021.121950

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The new non-proteinogenic amino acids with methylenebisphosphonic acids moieties are synthesized for the first time via unique reaction of tris(trimethylsilyl) phosphite and various N-formyl amino acids at the presence of effective catalyst - trimethylsilyl triflate under mild conditions . The further treatment of initially formed trimethylsilyl intermediates with the methanol excess resulted in the water-soluble non-proteinogenic amino acids with methylenebisphosphonic acids moieties in high yields. The catalytic scheme of target substances formation is proposed and discussed in detail. The structures of target functionalized amino acids and their precursors were confirmed by the H-1, C-13, P-31 NMR spectra and high resolution mass spectra. The resulted compounds are of great interest as promising antiviral substances and effective ligands. (C) 2021 Elsevier B.V. All rights reserved.

引用

页数：6

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