110270-13-8Relevant articles and documents
Heterocyclic Compounds from Sugars, XV: On the Configuration of Chiral C-2 Substituted 1,3-Thiazolidine-4-carboxylic Acids. Chirality Transfer to C-3 of 3,4-Dihydro-1H-pyrrolothiazoles
Gyoergydeak, Z.,Szilagyi, L.,Kajtar, J.,Argay, G.,Kalman, A.
, p. 189 - 208 (2007/10/02)
5-Substituted 3,4-dihydro-pyrrolothiazole-6,7-dicarboxylic acid esters 3 are obtained from 2-substituted-3-acyl-1,3-thiazolidine-4-carboxylic acids, 1 in -cycloaddition reactions via mesoionic oxazolone ("muenchnone") intermediates.The chirali
Thiazolidine-4(R)-carboxylic acids derived from sugars: Part I, C2-epimerisation in aqueous solutions.
Radomski, Jan,Temeriusz, Andrzej
, p. 223 - 238 (2007/10/02)
Reactions of L-cysteine (1) with L-xylose, D-ribose, D-lyxose, D-arabnose, D-glucose, L-rhamnose, and-fucose in aqueoes ethanol yielded crystalline 2(S)-(polihydroxyalkyl)thiazolidine-4(R)-carboxylic acids.Likewise, glycolaldehyde and L-glyceraldehyde, D-xylose, L-arabinose, D-mannose, D-galactose, and D-fucose gave crystalline 2(R),4(R) epimers.The reaction of 1 and D-glycerinaldehyde gave a syrup mixture of 2(S),4(R) and 2(R),4(R) compounds.The same substrates, but with no ethanol present, gave the 2(S),4(R) epimers for glycolaldehyde, L-xylose, L-fucose, and L-arabinose, and the 2(R),4(R) epimers for D-lyxose, L-rhamnose, D-mannose, Dgalactose, and D-fucose.The reactions of D-ribose, D-arabinose, D-xylose, and D-glucose gave sirupy mixtures of epimers.The crystalline reaction products, when dissolved in water, undergo rapid epimerisation as reflected by mutarotation and changes in the 1H- and 13C-n.m.r. spectra.