A Convenient Route to O-Glycosyl Lactates via Conjugate Addition to 2-Nitroglycals: Ring Closure to Novel Pyrano[2.3-b][1,4]-oxazines

Synthesis

Volumn , Issue 1, 2004, Pages 53-58

  Khodair, Ahmed I ^b   Pachamuthu, Kandasamy ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

^b TANTA UNIVERSITY   (Egypt)

Author keywords

Azadioxadecalines; Bicyclic systems; Glycal; Glycosides; Michael additions; Nitroolefin; Peptide mimetic

Indexed keywords

AROMATIC COMPOUNDS; ESTERS; NITROGEN COMPOUNDS; POLYPEPTIDES;

RING CLOSURE PROCESS;

SYNTHESIS (CHEMICAL);

3,4,6 TRI O BENZYL 2 NITROGALACTAL; 3,4,6 TRI O BENZYL 2 NITROGLUCAL; AMINE; BENZYL DERIVATIVE; BICYCLO COMPOUND; DIPEPTIDE; ESTER; LACTIC ACID; NITRO DERIVATIVE; OXAZINE DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONJUGATE; ISOMER; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0346057830     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42494     Document Type: Article

References (20)

1. For a review on glycosy 1 amino acids and carbohydrate based peptide mimetics see: Schweizer, F. Angew. Chem. Int. Ed. 2002, 41, 230; Angew. Chem. 2002, 114, 240; and references therein.
2. For a review on glycosy 1 amino acids and carbohydrate based peptide mimetics see: Schweizer, F. Angew. Chem. Int. Ed. 2002, 41, 230; Angew. Chem. 2002, 114, 240; and references therein.
3. Some related structures have been thus far reported as degradation products of natural compounds: (a) Stortz, C. A.; Chermiak, A.; Jones, R. G.; Treber, T. D.; Reinhardt, D. J. Carbohydr. Res. 1990, 207, 101. (b) Linkhardt, R. J.; Loganathan, D.; Al-Hakim, A.; Wang, H.-M.; Walenga, J. M.; Hoppensteadt, D.; Fareed, J. J. Red. Chem. 1990, 33, 1539.
4. Some related structures have been thus far reported as degradation products of natural compounds: (a) Stortz, C. A.; Chermiak, A.; Jones, R. G.; Treber, T. D.; Reinhardt, D. J. Carbohydr. Res. 1990, 207, 101. (b) Linkhardt, R. J.; Loganathan, D.; Al-Hakim, A.; Wang, H.-M.; Walenga, J. M.; Hoppensteadt, D.; Fareed, J. J. Red. Chem. 1990, 33, 1539.
5. (a) Das, J.; Schmidt, R. R. Eur. J. Org. Chem. 1998, 1609.
6. (b) Winterfeld, G. A.; Ito, Y.; Ogawa, T.; Schmidt, R. R. Eur. J. Org. Chem. 1999, 1167.
7. (c) Winterfeld, G. A.; Schmidt, R. R. Angew. Chem. Int. Ed. 2001, 40, 2654; Angew. Chem. 2001, 113, 2718.
8. (c) Winterfeld, G. A.; Schmidt, R. R. Angew. Chem. Int. Ed. 2001, 40, 2654; Angew. Chem. 2001, 113, 2718.
9. (d) Winterfeld, G. A.; Khodair, A. I.; Schmidt, R. R. Eur. J. Org. Chem. 2003, 1009.
10. (e) Khodair, A. I.; Winterfeld, G. A.; Schmidt, R. R. Eur. J. Org. Chem. 2003, 1847.
11. (f) Reddy, B. G.; Vankar, Y. D. Tetrahedron Lett. 2003, 44, 4765.
12. Winterfeld, G. A.; Das, J.; Schmidt, R. R. Eur. J. Org. Chem. 2000, 3047.
13. Pachamuthu, K.; Gupta, A.; Das, J.; Schmidt, R. R.; Vankar, Y. D. Eur. J. Org. Chem. 2002, 1479.
14. Bovin, N. V.; Zurabyan, S. E.; Khorlin, A. Y. Carbohydr. Res. 1981, 87, 25.
15. Lemieux, R. U.; Nagabushan, T. L.: Gunner, S. W. Can. J. Chem. 1968, 46, 405.
16. Holzapfel, C. W.; Marais, C. F.; van Dyk, M. S. Synth. Commun. 1988, 18, 97.
17. (a) Takamoto, T.; Sudoh, R.; Nakagawa, T. Carbohydr. Res. 1973, 27, 135.
18. (b) Sakakibara, T.; Tachimori, Y.; Sudoh, R. Tetrahedron Lett. 1982, 23, 5545.
19. Nishimura, S. Bull. Chem. Soc. Jpn. 1959, 32, 61.
20. This compound is commercially available.