- N-{[(IR,4S,6R-3-(2-PYRIDINYLCARBONYL)-3-AZABICYCLO [4.1.0] HEPT-4-YL] METHYL}-2-HETEROARYLAMINE DERIVATIVES AND USES THEREOF
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This invention relates to N-{[(1S,4S,6S)-3-(2-pyridinylcarbonyl)-3-azabicyclo[4.1.0]hept-4-yl]methyl}-2-heteroarylamine derivatives and their use as pharmaceuticals.
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Page/Page column 19; 20
(2010/06/20)
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- A new entry to polyfunctionalized 4,5-trans disubstituted oxazolidin-2-ones from L-aspartic acid
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A straightforward synthesis of enantiomerically pure (4R,5S)-5-oxazolidinecarboxylic acid, 2-oxo-4-[(t-butyldimethyl-silyloxy)methyl]-, benzyl ester and of (4S,5S)-4-oxazolidinecarboxylic acid, 2-oxo-5-[(t-butyldimethylsilyloxy)methyl]-, benzyl ester was envisaged starting from readily available L-aspartic acid. The key step is the diastereoselective addition of iodine with the introduction of a new stereogenic centre.
- Luppi, Gianluigi,Tomasini, Claudia
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p. 797 - 800
(2007/10/03)
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- Introduction of 4(S)-oxazolidineacetic acid, 2-oxo (D-Oxac) motif in a polypeptide chain: Synthesis and conformational analysis
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A four step synthesis of 4(S)-oxazolidineacetic acid, 2-oxo benzyl ester (D-Oxac-OBn) from L-Asp-OH in 45% overall yield is reported. The formation of by-products is completely avoided, by microwave irradiation and by the use of caesium carbonate as base. Moreover the synthesis and IR and 1H NMR conformational analysis of the tetramers Boc-L-Val-D-Oxac-L-Ala-OBn and Boc-L-Val-D-Oxac-Aib-L-Ala-OBn in solution is reported.
- Luppi, Gianluigi,Villa, Marzia,Tomasini, Claudia
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p. 247 - 250
(2007/10/03)
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- Enantioselective synthesis of 2-isocephem and 2-isooxacephem antibiotics
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The azido lactone 8 was prepared in a highly stereoselective manner by introduction of an azide function to the lactone 6 derived from L-aspartic acid, and then was converted into (2S,3S)-3-amino-2-azido-4-hydroxybutanoic acid 4. Four-component condensation of the amino acid 4, p-nitrobenzyl isocyanide and formaldehyde or 2,2-diethoxyacetaldehyde furnished the corresponding 3,4-cis-azetidinone 16 or 26 in excellent yield. 3-Methoxy-2-isooxacephalosporin was prepared by the intramolecular acylation of imidazolide 23 derived from compound 16. 3-Unsubstituted 2-isocephem and 2-isooxacephem analogues were prepared from the azetidinone 26.
- Nitta, Hajime,Ueda, Ikuo,Hatanaka, Minoru
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p. 1793 - 1798
(2007/10/03)
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- Cleavage of MEM ethers by tetrahalozincate reagents
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A modification of the zinc halide-mediated removal of the MEM group is described. By the expedient of adding two molar equivalents of ethereal hydrogen chloride or of lithium halide, the method is extended to substrates which otherwise chelate the zinc reagent without undergoing deprotection. The compatibility of the resulting reagent Systems with other functional groups is demonstrated, and examples are presented where deprotection of mono-MEM-protected 1,2- and 1,3-diols can be carried out, avoiding the cyclisation which occurs normally.
- Herbert, John M.,Knight, Julian G.,Sexton, Brian
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p. 15257 - 15266
(2007/10/03)
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- Selective Reduction of Nα-Protected Dicarboxylic Amino Acid Anhydrides into Corresponding Protected Amino Alcohols
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Nα-Protected dicarboxylic amino acid anhydrides, such as those of Z-D-Asp or Z-D-Glu have been selectively reduced in excellent yields with NaBH4 to give the corresponding Nα-protected amino alcohols.A probable mechanism for the sele
- Kundu, B.,Srivastava, V. P.,Mathur, K. B.
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