Home Physical Sciences Endogenous Alkaloids in Man, Part 33. Dimethyl (2S,4S)-and (2R,4S)-5,5-Dimethyl-1,3-thiazolidine-2,4-dicarboxylates, Two Diastereomeric Glyoxylate-Derived Heterocycles
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Endogenous Alkaloids in Man, Part 33. Dimethyl (2S,4S)-and (2R,4S)-5,5-Dimethyl-1,3-thiazolidine-2,4-dicarboxylates, Two Diastereomeric Glyoxylate-Derived Heterocycles

  • Gerhard Bringmann EMAIL logo , Doris Feineis , Wael Saeb , Christiana Hesselmann , Eva-Maria Peters and Karl Peters
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 55 Issue 2

Both title compounds were obtained in stereochemically pure form by refluxing 5,5-dim ethyl-1 ,3-thiazolidine-2,4-dicarboxylic acid (3) with methanolic HCl, followed by a separation of the two diastereomers 4a and 4b on silica gel. The X-ray structure analyses of these stereoisomers confirm the relative configuration to be cis for 4a and trans for 4b with respect to the two carboxymethyl substituents at C(2) and C(4). For both molecules, an envelopetype conformation of the thiazolidine ring was found with C(5)-S(1)-C(2)-N(3) being located in a plane showing a small ring torsion angle of -11.2° and -3.1° for the cis- and the rrafts-epimer, respectively. The trans-configured compound 4b adopts a nearly ideal envelope conformation with C(4) being the flap atom, while the cis-isomer 4a. apparently because of steric interactions of the C(2) and C(4) substituents, shows a twisted envelope conformation.

: Crystal Structure; Glyoxylate-Derived 1,3-Thiazolidines
Received: 1999-12-13
Published Online: 2014-6-2
Published in Print: 2000-2-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Sila-Substitution of the α-Amino Acid Proline: Synthesis of rac- and (R)-4,4-Dimethyl-4-sila-proline Ethyl Ester
  2. Synthesis and Crystal Structures of ATi[Nb6Cl18] Compounds (A = K, Rb, Cs, In, Tl)
  3. Optisch aktive Übergangsmetall-Komplexe, 122. Synthese von Palladium(II)-Schiff-Base-Komplexen -intramolekulare Wechselwirkungen / Optically Active Transition Metal Complexes, 122. Synthesis of Palladium (II) Complexes with Schiff Base Ligands -Intramolecular Interactions
  4. Intermetallic Cerium Compounds with Ordered U3Si2 Type Structure
  5. Electrochemical Synthesis of a 6-Coordinate Cadmium(II) Complex with N-Methylisatin N(4)-cyclohexylthiosemicarbazone
  6. Synthese und Kristallstruktur des Bromdifluormethyl-triphenyl- phosphoniumbromids, [(C6H5)3PCF2Br]+ Br- / Synthesis and Crystal Structure of Bromodifluoromethyl-triphenylphosphonium Bromide, [(C6H5)3PCF2Br]+ Br-
  7. Synthesis, Structure and Properties of Poly > [(N-(2-Hydroxyethyl)- N'-carboxymethyl-1,2-ethylenediamine-N, N'-Diacetato)copper(II) Hydrate], {[Cu(Hhedta)] · H2O }n
  8. Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalyse von cis-(n-Bu4N)2[ReBr4(NCS)2 ], cis-(n-Bu4N)2[ReBr4(NCSe)2] und cis-(n-Bu4N)2[ReBr4(NCS)(NCSe)] / Crystal Structures, Vibrational Spectra and Normal Coordinate Analyses of cis-(n-Bu4N)2[ReBr4(NCS)2], cis-(n-Bu4N)2[ReBr4(NCSe)2,] and cis -(n -Bu4N)2[ReBr4(NCS)(NCSe)]
  9. Bis(diphenylphosphanyl)amine and its Disulfide and Diselenide. Application of the INEPT-HEED Pulse Sequence for Measurement of 1J(31P, 15N) and Isotope Induced Chemical Shifts 1⊿ 14/15N(31P) at Natural Abundance of 15N
  10. Synthesis, Multinuclear (1H, 13C and 17O ) Magnetic Resonance Spectroscopy and Conformational Analysis of Some Substituted Aryl Naphthoates
  11. Substituent Influences on the Keto-Enol Tautomerism in 1-(2-Hydroxyphenyl)-3-α-and -β-naphthylpropane-1,3-diones Monitored by 1H and 13C NMR Spectroscopy
  12. Chiral Aryl Sulfonyl Hydantoins as Hypoglycemic Agents
  13. Endogenous Alkaloids in Man, Part 33. Dimethyl (2S,4S)-and (2R,4S)-5,5-Dimethyl-1,3-thiazolidine-2,4-dicarboxylates, Two Diastereomeric Glyoxylate-Derived Heterocycles
  14. The Inclusion of Carbon Disulfide in p-tert-Butylcalix[4]-and [6 ]arene - A Combined Crystallographic and Vibrational Spectroscopic Study
  15. Facile Regioselective Synthesis of 1,2,6,8-Tetraazaspiro[4.4]nona-2,6-dien-9-ones
  16. A New Triterpenoidal Saponin from the Bark of Guaiacum officinale L.
  17. Alternative Method for the Preparation of 4,5-Ethylenedithio-1,3-dithiole-2- thione and Related Compounds
  18. A Diterpenoid with a New Modified Abietane Skeleton from Salvia palaestina
https://doi.org/10.1515/znb-2000-0213

Articles in the same Issue

  1. Sila-Substitution of the α-Amino Acid Proline: Synthesis of rac- and (R)-4,4-Dimethyl-4-sila-proline Ethyl Ester
  2. Synthesis and Crystal Structures of ATi[Nb6Cl18] Compounds (A = K, Rb, Cs, In, Tl)
  3. Optisch aktive Übergangsmetall-Komplexe, 122. Synthese von Palladium(II)-Schiff-Base-Komplexen -intramolekulare Wechselwirkungen / Optically Active Transition Metal Complexes, 122. Synthesis of Palladium (II) Complexes with Schiff Base Ligands -Intramolecular Interactions
  4. Intermetallic Cerium Compounds with Ordered U3Si2 Type Structure
  5. Electrochemical Synthesis of a 6-Coordinate Cadmium(II) Complex with N-Methylisatin N(4)-cyclohexylthiosemicarbazone
  6. Synthese und Kristallstruktur des Bromdifluormethyl-triphenyl- phosphoniumbromids, [(C6H5)3PCF2Br]+ Br- / Synthesis and Crystal Structure of Bromodifluoromethyl-triphenylphosphonium Bromide, [(C6H5)3PCF2Br]+ Br-
  7. Synthesis, Structure and Properties of Poly > [(N-(2-Hydroxyethyl)- N'-carboxymethyl-1,2-ethylenediamine-N, N'-Diacetato)copper(II) Hydrate], {[Cu(Hhedta)] · H2O }n
  8. Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalyse von cis-(n-Bu4N)2[ReBr4(NCS)2 ], cis-(n-Bu4N)2[ReBr4(NCSe)2] und cis-(n-Bu4N)2[ReBr4(NCS)(NCSe)] / Crystal Structures, Vibrational Spectra and Normal Coordinate Analyses of cis-(n-Bu4N)2[ReBr4(NCS)2], cis-(n-Bu4N)2[ReBr4(NCSe)2,] and cis -(n -Bu4N)2[ReBr4(NCS)(NCSe)]
  9. Bis(diphenylphosphanyl)amine and its Disulfide and Diselenide. Application of the INEPT-HEED Pulse Sequence for Measurement of 1J(31P, 15N) and Isotope Induced Chemical Shifts 1⊿ 14/15N(31P) at Natural Abundance of 15N
  10. Synthesis, Multinuclear (1H, 13C and 17O ) Magnetic Resonance Spectroscopy and Conformational Analysis of Some Substituted Aryl Naphthoates
  11. Substituent Influences on the Keto-Enol Tautomerism in 1-(2-Hydroxyphenyl)-3-α-and -β-naphthylpropane-1,3-diones Monitored by 1H and 13C NMR Spectroscopy
  12. Chiral Aryl Sulfonyl Hydantoins as Hypoglycemic Agents
  13. Endogenous Alkaloids in Man, Part 33. Dimethyl (2S,4S)-and (2R,4S)-5,5-Dimethyl-1,3-thiazolidine-2,4-dicarboxylates, Two Diastereomeric Glyoxylate-Derived Heterocycles
  14. The Inclusion of Carbon Disulfide in p-tert-Butylcalix[4]-and [6 ]arene - A Combined Crystallographic and Vibrational Spectroscopic Study
  15. Facile Regioselective Synthesis of 1,2,6,8-Tetraazaspiro[4.4]nona-2,6-dien-9-ones
  16. A New Triterpenoidal Saponin from the Bark of Guaiacum officinale L.
  17. Alternative Method for the Preparation of 4,5-Ethylenedithio-1,3-dithiole-2- thione and Related Compounds
  18. A Diterpenoid with a New Modified Abietane Skeleton from Salvia palaestina
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