Chemical and enzymatic diastereoselective cleavage of β-D galactopyranosylsulfoxides

Tetrahedron Letters

Volumn 38, Issue 47, 1997, Pages 8267-8270

  Khiar, Noureddine ^a   Alonso, Inés ^b   Rodriguez, Natividad ^c   Fernandez Mayoralas, Alfonso ^d   Jimenez Barbero, Jesus ^d   Nieto, Ofelia ^d   Cano, Felix ^d   Foces Foces, Concepción ^d   Martin Lomas, Manuel ^d  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^c UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

BETA GALACTOSIDASE; GALACTOSE; PYRANOSIDE; SULFINIC ACID DERIVATIVE; SULFOXIDE; THIOGLYCOSIDE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; HYDROLYSIS; OXIDATION; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0030701646     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10164-2     Document Type: Article

References (17)

1. For the use of chiral sulfoxides in asymmetric synthesis see for examples: (a) Posner, G. H., in The Chemistry of Sulfones and Sulfoxides, ed. Patai, S., Rappoport, Z. and Stirling, C. J. M. 1988, pp 823.
2. (b) Solladié, G. Synthesis, 1981, 185.
3. (c) Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123.
4. (d) Carreño, M. C. Chem. Rev. 1995, 95, 1717.
5. Yan, L.; Taylor, C. M.; Goodnow, R. Jr.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953, and references cited therein.
6. Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580.
7. For the use of triflic acid as promoter in the sulfoxide glycosylation reaction see Alonso, I.; Khiar, N.; Martin-Lomas, M. Tetrahedron Lett., 1996, 37, 1477.
8. th International Carbohydrate Symposium hold in Ottawa, Canada, July 7-24, 1994 : Khiar, N.; Fernandez-Mayoralas, A.; Nieto, O.; Martin Lomas, M.; poster n° B 2.62.
9. (a) Glass, R. S.; Setzer, W. N.; Prabhu, U. D. G.; Wilson, G. S. Tetrahedron Lett. 1982, 23, 2335.
10. (b) De Lucchi, O.; Lucchini, V. Marchioro, C; Valle, G.; Modena, G. J. Org. Chem. 1986, 51, 1457
11. For leading references on the directing effect of the hydroxy group in the oxidation of sulfides see: Hirschon, A. S.; Doi, J. T.; Musker, W. K. J. Am. Chem. Soc. 1982, 104, 725; Klein, J.; Stollar, H. Tetrahedron Lett. 1974, 30, 2541.
12. For leading references on the directing effect of the hydroxy group in the oxidation of sulfides see: Hirschon, A. S.; Doi, J. T.; Musker, W. K. J. Am. Chem. Soc. 1982, 104, 725; Klein, J.; Stollar, H. Tetrahedron Lett. 1974, 30, 2541.
13. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G; Hendrickson, T; Still, W. C. J. Comput. Chem. 1990, 11, 440.
14. Khiar, N.; Martin-Lomas, M. J. Org. Chem. 1995, 60, 7017.
15. A full paper including details of the X-ray analysis and molecular mechanics calculation will be published elsewhere
16. Cano, F. H.; Foces-Foces, C.; Bernabe, M.; Jimenez-Barbero, J.; Martin-Lomas, M.; Penades, S. Tetrahedron, 1985, 41, 3875.
17. Karthaus, O.; Shoda, S.; Kobayashi, S. Tetrahedron Asymmetry, 1994, 5, 2213.