Synthesis of 2-deoxy-4-octulose derivatives by highly diastereoselective alkylations of protected hexuloses

Tetrahedron Asymmetry

Volumn 8, Issue 15, 1997, Pages 2597-2606

  Izquierdo, Isidoro ^a   Plaza, María T ^a   Robles, Rafael ^a   Mota, Antonio ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030874265     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00266-8     Document Type: Article

References (15)

1. Izquierdo Cubero, I.; Plaza López-Espinosa, M.-T.; Rodríguez Alonso, M.; Asenjo Asenjo, R.; Ramírez Fernández, A., J. Org. Chem., 1997, in press.
2. Burgess, K.; Henderson, I., Tetrahedron, 1992, 48, 4045-4066, and references therein.
3. Izquierdo Cubero, I.; Plaza López-Espinosa, M.-T.; Robles Díaz, R.; Rodríguez Melgarejo, C., Tetrahedron: Asymmetry, 1996, 7, 3593-3604.
4. Payne, G. B., J. Org. Chem., 1969, 33, 3517-3523.
5. Izquierdo Cubero, I.; Plaza López-Espinosa, M.-T., Carbohydr. Res., 1990, 205, 393-304.
6. Izquierdo Cubero, I.; Plaza López-Espinosa, M.-T.; Kari, N., Carbohydr. Res., 1994, 261, 231-242.
7. Han, B.-H.; Boudjouk, P., J. Org. Chem., 1982, 47, 5030-5032.
8. Rathke, M. W.; Sullivan, D. F., J. Am. Chem. Soc., 1973, 95, 3050-3051.
9. Johnson, A. W.; Amel, R. T., J. Org. Chem., 1969, 34, 1240-1247.
10. Viti, S. M., Tetrahedron Lett. 1982, 23, 4541-4544.
11. Hirst, E. L.; Percival, E., Methods Carbohydr. Chem., 1963, 2, 145-150.
12. Purdie, T.; Williamson, S., J. Chem. Soc. 1895, 67, 957-982.
13. Computerized representation of the most stable conformations for 1 and 10, calculated with the TRIPOS force field.
14. Clark, M.; Cramer III, R. D.; Van Opdenbosch, N., J. Comput. Chem. 1989, 10, 982.
15. TRIPOS force field is implemented in the SYBYL 6.1 program, available from Tripos Inc. 1699 S. Hanley Road, St. Louis, Missouri 63144-2913, USA.