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Literature DB >> 18037974

New access to H-phosphonates via metal-catalyzed phosphorus-oxygen bond formation.

Laëtitia Coudray¹, Isabelle Abrunhosa-Thomas, Jean-Luc Montchamp.

Abstract

A novel approach to H-phosphonates from hypophosphorous acid using a transfer hydrogenation process was developed. This method is atom-economical, environmentally friendly, catalytic, and efficient, leading easily to H-phosphonate monoesters or ammonium salt in moderate to good yields.

Entities: Chemical

Year: 2007 PMID： 18037974 PMCID： PMC2084078 DOI： 10.1016/j.tetlet.2007.07.057

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

12 in total

1. Synthesis and biological evaluation of isomeric dinucleoside monophosphates and monomethylphosphonates of 9-beta-D-arabinofuranosyladenine and related analogues.

Authors: F Puech; G Gosselin; J qalzarini; E De Clercq; J L Imbach
Journal: J Med Chem Date: 1988-10 Impact factor: 7.446

2. Comparison of the antiviral activity of hydrophobic amino acid phosphoramidate monoesters of 2'3'-dideoxyadenosine (DDA) and 3'-azido-3'-deoxythymidine (AZT).

Authors: S L Chang; G Griesgraber; C R Wagner
Journal: Nucleosides Nucleotides Nucleic Acids Date: 2001-08 Impact factor: 1.381

Review 3. How to get the most out of two phosphorus chemistries. Studies on H-phosphonates.

Authors: Jacek Stawinski; Adam Kraszewski
Journal: Acc Chem Res Date: 2002-11 Impact factor: 22.384

4. Synthesis, in vitro anti-breast cancer activity, and intracellular decomposition of amino acid methyl ester and alkyl amide phosphoramidate monoesters of 3'-azido-3'-deoxythymidine (AZT).

Authors: V V Iyer; G W Griesgraber; M R Radmer; E J McIntee; C R Wagner
Journal: J Med Chem Date: 2000-06-01 Impact factor: 7.446

5. Nucleotides and pronucleotides of 2,2-bis(hydroxymethyl)methylenecyclopropane analogues of purine nucleosides: synthesis and antiviral activity.

Authors: Zhaohua Yan; Earl R Kern; Elizabeth Gullen; Yung-Chi Cheng; John C Drach; Jiri Zemlicka
Journal: J Med Chem Date: 2005-01-13 Impact factor: 7.446

New access to H-phosphonates via metal-catalyzed phosphorus-oxygen bond formation.

1. Synthesis and biological evaluation of isomeric dinucleoside monophosphates and monomethylphosphonates of 9-beta-D-arabinofuranosyladenine and related analogues.

2. Comparison of the antiviral activity of hydrophobic amino acid phosphoramidate monoesters of 2'3'-dideoxyadenosine (DDA) and 3'-azido-3'-deoxythymidine (AZT).

Review 3. How to get the most out of two phosphorus chemistries. Studies on H-phosphonates.

4. Synthesis, in vitro anti-breast cancer activity, and intracellular decomposition of amino acid methyl ester and alkyl amide phosphoramidate monoesters of 3'-azido-3'-deoxythymidine (AZT).

5. Nucleotides and pronucleotides of 2,2-bis(hydroxymethyl)methylenecyclopropane analogues of purine nucleosides: synthesis and antiviral activity.

6. Synthesis and anticancer activities of amphiphilic 5-fluoro-2'-deoxyuridylic acid prodrugs.

7. NiCl2-catalyzed hydrophosphinylation.

8. Palladium-catalyzed hydrophosphinylation of alkenes and alkynes.

9. Synthesis of DNA via deoxynucleoside H-phosphonate intermediates.

10. H-phosphonate derivatives as novel peptide deformylase inhibitors.

1. Synthesis and in vitro evaluation of aspartate transcarbamoylase inhibitors.

Review 2. Let's Make White Phosphorus Obsolete.