- Composition on the basis of phosphonoacetic acid. Synthesis and antiviral activity
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A manufacturable technology for the production of an antiviral composition containing phosphonoacetic acid, involing PH-alkylation of dimethyl phosphite with methyl chloroacetate under phase-transfer conditions and subsequent in situ hydrolysis of the intermediate product, was developed. The composition showed expressed antiviral effect against herpesviral infections caused by herpes simplex virus 1 and 2 and cytomegalovirus. The composition in the effective concentration range was found to exhibit no cytotoxic effect on VERO green monkey kidney and M-19 human diploid cell cultures. The resulting data suggest potential uses of the composition as an antiviral agent in practical medicine and as an antiviral additive to synthetic detergents for sanitation in health care and food production facilities.
- Alimbarova,Kharlamov,Bondarenko,Barinskii
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p. 2441 - 2448
(2015/11/24)
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- A facile synthesis of novel chiral phosphonoacetates bearing a stereogenic phosphorus atom
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Novel chiral phosphonoacetates bearing a stereogenic phosphorus atom were successfully synthesized by enzyme-catalyzed kinetic resolution of racemic phosphonoacetates.
- Sano, Shigeki,Kujime, Eiko,Takemoto, Yuka,Shiro, Motoo,Nagao, Yoshimitsu
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p. 131 - 134
(2007/10/03)
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- Intramolecular cyclopropanation reactions en route to novel P- heterocycles
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The first examples of intramolecular cyclopropanation reactions on a phosphonate template catalyzed by Rh2(OAc)4 are described. These reactions proceed in excellent yield and give mixtures of the P-heterocycles cis-2a-d and trans-2a-d with moderate levels of diastereoselectivity. The diastereoselectivity of this transformation is dependent upon the size of the alkyl group R contained in the alkyl α-diazodiallylphosphonoacetate starting materials 1a-d.
- Hanson, Paul R.,Sprott, Kevin T.,Wrobleski, Aaron D.
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p. 1455 - 1458
(2007/10/03)
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- Electronic effects on the Z(cis)-selectivity of Horner-Wadsworth-Emmons olefination reaction
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Various phosphorates have been synthesized to study the Horner-Wadsworth-Emmons olefination reaction. The phosphoryl stabilised carbanion resulting from phosphonates, carrying electron withdrawing groups attached to phosphorus atom, has been reacted with a variety of aldehydes at - 78°C leading to Z(cis) selective olefination.
- Mahipal Reddy,Raj Gopal,Jayathirtha Rao
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p. 312 - 317
(2007/10/03)
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- INSERTION OF CARBENES INTO P-H BONDS. 5. SYNTHESIS OF NEW PHOSPHONATES AND PHOSPHINATES IN REACTIONS CATALYSED BY Cu, Pd, Rh, Ni COMPLEXES
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Cu(OTf)2 and Cu(acac)2 were found to be the most effective catalysts in the reaction of diazo compounds Ph2CN2 (1a), EtOC(O)CHN2 (1b), MeOC(O)CHN2 (1c), MeC(O)CN2C(O)OMe (1d), ClCH2C(O)CHN2 (1e) and CH2N2 (1f) with hydrophosphoryl compounds (MeO)2P(O)H (2a), (t-BuO)2P(O)H (2b), Ph(MeO)P(O)H (2c), (EtO)2P(O)H (2d) and P(O)H (2e) resulting in P-C bond formations.Cu, Pd and Rh acetates and Ni(acac)2 have a much lower efficiency.Chlorines in Cl3CC(O)CH2P(O)(OMe)2 (3k) and Cl2CHC(O)CH2P(O)(OMe)2 (3l) are reduced in the copper catalysed Atherton-Todd reaction.Key words: Catalyst; diazo compound; hydrophosphoryl compound; insertion; phosphonate; phosphinate.
- Polozov, Alexander M.,Mustaphin, Albert H.,Khotinen, Alexander V.
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p. 153 - 160
(2007/10/02)
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- Tricyclo{6.2.1.01,6 }undecanes useful as fragrance chemicals
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Novel tricycloundecanones are disclosed having the general formula STR1 wherein R1, R2, and R3 are hydrogen or 1 to 3 carbon alkyl groups having a total carbon number of six or less. These compounds are useful perfumery ingredients characterized by odors of the woody type. Useful derivatives of the compounds are also disclosed as well as a novel procedure for preparation thereof.
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- On the Successive Enveloping of the Benzene Nucleus with Saturated Rings
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Starting with benzosuberone (3) the tri- up to hexacyclic ketones 4-7 are prepared by successive annulations, requiring three single steps in each case, 1) carbonyl olefination to yield the unsaturated esters 9, 13, 15, and 17, 2) reduction with NaBH4/NiCl2 to give the corresponding saturated esters (or acids, respectively) 11, 14, 16, and 18, and 3) cyclization with trifluoroacetic acid/trifluoroacetic anhydride.Concluding reactions of the sterically unresolved hexacyclic ketone 7 with methylenetriphenylphosphorane yield the exomethylene derivative 19 as mixtures of diastereomers with varying composition.Attemps to the final cyclization and dehydrogenation of 19 produced only tar- and coal-like materials.
- Hellwinkel, Dieter,Kosack, Thomas
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p. 226 - 238
(2007/10/02)
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