- Synthesis of unnatural 2- and 3-deoxyfuranose analogues
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This Letter describes the synthesis of two racemic analogues of unnatural 3′-deoxy and 2′-deoxy sugars, where a phosphorus atom replaces the carbon atom in the 2′- or 3′-position. Two methods of four- and 5-steps were developed affording these new unnatur
- Dayde, Bénédicte,Pierra, Claire,Gosselin, Gilles,Surleraux, Dominique,Ilagouma, Amadou Tidjani,Van Der Lee, Arie,Volle, Jean-No?l,Virieux, David,Pirat, Jean-Luc
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- Novel cyclic phosphinic acids as GABAC ρ receptor antagonists: Design, synthesis, and pharmacology
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Understanding the role of GABAC receptors in the central nervous system is limited due to a lack of specific ligands. Novel γ-aminobutyric acid (GABA) analogues based on 3-(aminomethyl)-1-oxo-1-hydroxy-phospholane 17 and 3-(guanido)-1-oxo-1-hydroxy-phospholane 19 were investigated to obtain selective GABAC receptor antagonists. A compound of high potency (19, KB = 10 μM) and selectivity (greater than 100 times at ρ1 GABAC receptors as compared to α 1β2γ2L GABAA and GABAB(1b,2) receptors) was obtained. The cyclic phosphinic acids (17 and 19) are novel lead agents for developing into more potent and selective GABAC receptor antagonists with increased lipophilicity for future in vivo studies.
- Gavande, Navnath,Yamamoto, Izumi,Salam, Noeris K.,Ai, Tu-Hoa,Burden, Peter M.,Johnston, Graham A. R.,Hanrahan, Jane R.,Chebib, Mary
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- Synthesis of H-Phosphonate Intermediates and Their Use in Preparing the Herbicide Glyphosate
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The esterfication of hypophosphorous acid is followed by reaction with another molecule of alcohol under the action of a nickel catalyst to provide a green method for the preparation of H-phosphonate diesters. This method avoids the need for any stoichiometric chlorine unlike those based on phosphorous trichloride.
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Paragraph 0046
(2014/10/16)
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- Organophosphorus chemistry without PCl3: A bridge from hypophosphorous acid to H-phosphonate diesters
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A process for the conversion of hypophosphorous acid (H3PO 2, HPA) and alcohols into various H-phosphonate diesters [(RO) 2P(O)H] is described. The new reaction provides a missing bridge between HPA and important H-phosphonates, completely avoiding the use of PCl3. Nickel chloride or nickel on silica catalyze the oxidative phosphorylation of alkyl phosphinates with various alcohols or water. The reaction is atom economic and avoids the formation of waste products. The previous need for both chlorine and base is completely avoided. Esterification of hypophosphorous acid followed by reaction with another molecule of alcohol under the action of a nickel catalyst provides a green method for the preparation of H-phosphonates. This method entirely avoids the need for any stoichiometric chloride unlike those based on phosphorus trichloride. Copyright
- Fisher, Henry C.,Prost, Lucie,Montchamp, Jean-Luc
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p. 7973 - 7978
(2014/01/06)
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- Synthesis of novel 5′-hydrogenphosphonothioate derivatives of AZT, d4T and ddI
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5′-hydrogenphosphonothioate derivatives of AZT, d4T, and ddI as anti-HIV prodrug candidates were synthesized in 61-76% yields under mild conditions through sequential one-pot reactions, i.e., couple of triethylammonium phosphinate with different alcohols
- Jin, Ying,Sun, Ming,Fu, Hua,Zhao, Yu-Fen
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p. 116 - 117
(2007/10/03)
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- A novel and convenient preparation of hypophosphite esters
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Only a few methods have been described for the preparation of hypophosphite esters (alkyl phosphinates, ROP(O)H2). As a result, comparatively few applications have been reported, and these intermediates have not been widely exploited in organop
- Deprèle, Sylvine,Montchamp, Jean-Luc
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p. 154 - 163
(2007/10/03)
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- Mono-and dialkylation of isopropyl phosphinate - A simple preparation of alkylphosphinate esters1
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Base-catalysed alkylation of isopropyl phosphinate with primary alkyl halides under mild conditions affords the corresponding alkyl phosphinate esters in fair to excellent yields.
- Gallagher, Michael J.,Ranasinghe, Millagahamada G.,Jenkins, Ian D.
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p. 255 - 259
(2007/10/03)
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- ON THE INTERACTION BETWEEN HYPOPHOSPHOROUS ACID AND ALCOHOLS
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The esterification of hypophosphorous acid with alcohols, i.e. isopropanol, isobutanol, n-pentanol, n-octanol and 1,3-propylene glycol leads to the formation of the corresponding phosphonous acid esters in yields of up to 50percent, in addition to the hypophosphorous acid esters.The compounds are characterized by their elemental analyses, infrared and 1H NMR spectra.A mechanism of their formation is suggested.
- Devedjiev, I.,Ganev, V.,Stefanova, R.,Borisov, G.
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