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Literature DB >> 12357751

A new synthesis of phosphoramidates: inhibitors of the key bacterial enzyme aspartate semi-aldehyde dehydrogenase.

Luke A Adams¹, Russell J Cox, Jennifer S Gibson, M Belén Mayo-Martín, Magnus Walter, William Whittingham.

Abstract

A new, mild and high yielding synthesis of phosphoramidates is described: potassium salts of carboxylic acids are treated with ethylchloroformate and the resulting activated anhydride-carbonates are then treated with LiNH-P(O)(OEt)2 in situ--the methodology is especially suited to acid sensitive systems featuring BOC, tBu or acetal protecting groups.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2002 PMID： 12357751 DOI： 10.1039/b206199f

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

6 in total

1. N-[Bis(dimethyl-amino)phosphinoyl]-2,2,2-trichloro-acetamide.

Authors: Oleksiy V Amirkhanov; Olesia V Moroz; Kateryna O Znovjyak; Elizaveta A Trush; Tetyana Yu Sliva
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-04-17

2. catena-Poly[sodium-di-μ-aqua-sodium-bis[μ-2,2,2-trichloro-N-(dimorpholinophosphoryl)acetamide]].

Authors: Olena O Litsis; Vladimir A Ovchynnikov; Tetyana Yu Sliva; Irina S Konovalova; Vladimir M Amirkhanov
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-03-20

3. Tris(N-{bis-[meth-yl(phen-yl)amino]-phosphor-yl}benzene-sulfonamidato-κ²O,O')(1,10-phenanthroline-κ²N,N')lanthanum(III).

Authors: Angelina Yu Prytula-Kurkunova; Victor A Trush; Viktoriya V Dyakonenko; Tetyana Yu Sliva; Vladimir M Amirkhanov
Journal: Acta Crystallogr E Crystallogr Commun Date: 2017-06-27

A new synthesis of phosphoramidates: inhibitors of the key bacterial enzyme aspartate semi-aldehyde dehydrogenase.

1. N-[Bis(dimethyl-amino)phosphinoyl]-2,2,2-trichloro-acetamide.

2. catena-Poly[sodium-di-μ-aqua-sodium-bis[μ-2,2,2-trichloro-N-(dimorpholinophosphoryl)acetamide]].

3. Tris(N-{bis-[meth-yl(phen-yl)amino]-phosphor-yl}benzene-sulfonamidato-κ²O,O')(1,10-phenanthroline-κ²N,N')lanthanum(III).

4. Crystal structure of N-(di-phenyl-phosphor-yl)-2-meth-oxy-benzamide.

5. Tetra-methyl N,N'-(2,2,3,3,4,4-hexa-fluoro-1,5-dioxopentane-1,5-di-yl)bis-(phospho-ramidate).

6. Synthesis and Evaluation of Biological Activity of New Arylphosphoramidates.

A new synthesis of phosphoramidates: inhibitors of the key bacterial enzyme aspartate semi-aldehyde dehydrogenase.

1. N-[Bis(dimethyl-amino)phosphinoyl]-2,2,2-trichloro-acetamide.

2. catena-Poly[sodium-di-μ-aqua-sodium-bis[μ-2,2,2-trichloro-N-(dimorpholinophosphoryl)acetamide]].

3. Tris(N-{bis-[meth-yl(phen-yl)amino]-phosphor-yl}benzene-sulfonamidato-κ2O,O')(1,10-phenanthroline-κ2N,N')lanthanum(III).

4. Crystal structure of N-(di-phenyl-phosphor-yl)-2-meth-oxy-benzamide.

5. Tetra-methyl N,N'-(2,2,3,3,4,4-hexa-fluoro-1,5-dioxopentane-1,5-di-yl)bis-(phospho-ramidate).

6. Synthesis and Evaluation of Biological Activity of New Arylphosphoramidates.

3. Tris(N-{bis-[meth-yl(phen-yl)amino]-phosphor-yl}benzene-sulfonamidato-κ²O,O')(1,10-phenanthroline-κ²N,N')lanthanum(III).