The synthesis of novel chiral cholic acid-based molecular clefts containing unsymmetrically disubstituted urea unit

Synthetic Communications

Volumn 33, Issue 17, 2003, Pages 3055-3061

  Mu, Qi Ming ^a   Xue, Cui Hua ^a   Zhang, Qing Hua ^a   Chen, Shu Hua ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Cholic acid; Disubstituted urea; Molecular cleft; Synthesis

Indexed keywords

CARBONIC ACID; CHOLIC ACID; DEOXYCHOLIC ACID DERIVATIVE; METHYL DEOXYCHOLATE; UNCLASSIFIED DRUG; UREA;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; INFRARED SPECTROMETRY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0041428218     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120022481     Document Type: Article

References (9)

1. (a) Rebek Jr, J. Model studies in molecular recognition. Science 1987, 235, 1478;
2. (b) Rebek Jr, J. Molecular recognition and biophysical organic chemistry. Acc. Chem. Res. 1990, 23, 399;
3. (c) Rebek Jr, J. Molecular recognition with model systems. Angew. Chem. Int. Ed. Engl. 1990, 29, 245.
4. D'souza, L.J.; Maitra, U. Design, synthesis, and evaluation of bile acid-based molecular tweezers. J. Org. Chem. 1996, 61, 9494.
5. Lawless, L.J.; Blackburn, A.G.; Ayling, A.G.; Nieves P'erez-Pay'an, M.; Davis, A.P. Steroidal guanidines as enantioselective receptors for N-acyl α-amino acids. Part 1. 3α-Guanylated carbamates derived from cholic acid. J. Chem. Soc.; Perkin Trans. 1. 2001, 1329.
6. Maitra, U.; Mathivanan, P. Diastereoselective reduction of α-keto esters derived from functionalized cholic acid. Tetrahedron: Asymmetry 1994, 5, 1171.
7. Xue, C.H.; Hu, R.; Mu, Q.M.; Li, F.; Chen, S.H. Enantioselective recognition of amino acid derivatives by chiral molecular tweezers derived from steroid cholic acid. Acta. Chimica Sinica 2000, 58, 717.
8. Xue, C.H.; Mu, Q.M.; Chen, S.H. Enantioselective recognition of carbamate-type molecular tweezers derived from deoxycholic acid for amino acid methyl esters. Acta. Chimica Sinica 2002, 60, 355.
9. Hu, R.; Zhao, Z.M.; Yang, Z.X.; Dai, Y.; Chen, S.H. Design and synthesis of molecular tweezers from hyodeoxycholic acid. J. Sichuan. University (Natural Science Edition). 1999, 36, 800.