30193-57-8Relevant academic research and scientific papers
Carbohydrates as Chiral Auxiliaries in Asymmetric Darzens Reactions: Enantioselective Synthesis of the Benzothiazepine Ring System of Diltiazem
Nangia, Ashwini,Rao, P. Bheema,Madhavi, N.N.L.
, p. 1716 - 1730 (2007/10/03)
Carbohydrate alcohols 11 and 14, prepared from D-glucose and D-galactose, are employed as their chloro acetes 18 and 19 in the asymmetric Darzens glycidic ester condensation with p-anisaldehyde.Alcohol 11 induces modest diastereoselectivity (65:35) and af
Novel optically active carboxylic acid derivative l-lysine salt and process for production thereof
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, (2008/06/13)
A novel salt of d-threo-2-hydroxy-3-(2-amino--phenylthio)-3-(4-methoxyphenyl)-propionic acid represented by the following formula (1) wherein C* represents the carbon atoms of the optically resolved molecules,with L-lysine. The above compound can be produced by reacting d1-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4--methoxyphenyl)-propionic acid with L-lysine or a metal salt of said propionic acid with an acid salt of L-lysine to form corresponding salts, and separating the difficult-ly-soluble salt from the resulting two optically active salts by utilizing the difference in solubility in a solvent between the two optically active salts. This compound is useful as a synthesis intermediate for a known pharmaceutical compound, diltiazem hydrochloride.
Reaction of 3-Phenylglycidic Esters. Part 1. Stereoselective Opening of the Oxirane Ring of trans-3-Phenylglycidic Esters with 2-nitrothiophenols and the Effects of Various Catalysts Thereon
Hashiyama, Tomiki,Inoue, Hirozumi,Konda, Mikihiko,Takeda, Mikio
, p. 1725 - 1732 (2007/10/02)
In the reaction of 2-nitrothiophenol (2) with trans-3-phenylglycidic esters carrying various substituents on the benzene ring, both reactivity and stereoselectivity of the oxirane ring-opening of the glycidates were markedly influenced by the electronic nature of the substituents.The presence of electron-donating groups was favourable for both reactivity and the preferential formation of cis-opening products, while the reverse was true for electron-withdrawing groups.As a result of our investigation on the catalytic effect of various Lewis acids in the reaction of the 4-methoxy derivative (1) with (2), tin compounds were found to be effective catalysts for cis-opening and readily produced the threo-nitro ester (3a), a key intermediate for the synthesis of diltiazem (5).Isolation of the crystalline complex (adduct A) from the reaction of (2) with SnCl4 and its efficient catalytic activity similar to that of SnCl4 suggest that the transition state involves co-ordination of tin derivatives both with (2) and the epoxy oxygen of (1) to cause highly specific cis-opening.
Process for preparing 1,5-benzothiazephine derivatives
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, (2008/06/13)
A process for preparing 1,5-benzothiazepine derivatives of the formula: STR1 wherein Ar is a phenyl substituted with a lower alkoxy, R is a lower alkyl, R1 and R2 are each a lower alkyl, and Y is a lower alkylene, which have excellent coronary vasodilating and psychoneurotic activities and are useful particularly as a Ca++ -antagonistic coronary vasodilator.
