Highly facialselective synthesis of pyranose 1,3-oxazines and their ring opening with nucleophiles: A novel entry to 2-c-branched glycosides

Organic Letters

Volumn 13, Issue 19, 2011, Pages 5088-5091

  Yin, Biao Lin ^a   Zhang, Ze Ren ^a   Xu, Li Wen ^b   Jiang, Huanfeng ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b HANGZHOU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; GLYCOSIDE; OXAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CARBON; GLYCOSIDES; MOLECULAR STRUCTURE; OXAZINES; STEREOISOMERISM;

EID: 80054773958     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2019604     Document Type: Article

References (39)

1. Chapleur, Y.; Chétien, F. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1997; p 207.
2. Yoshima, J. Adv. Carbohydr. Chem. Biochem. 1984, 42, 69.
3. Lindberg, B. Adv. Carbohydr. Chem. Biochem. 1987, 82, 279.
4. Celmer, W. D. Pure Appl. Chem. 1971, 28, 413.
5. Hanessian, S. Total Synthesis of Natural products: The Chiron Approach; Pergamon Press: Oxford, 1983.
6. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57.
7. Sasaki, M.; Inoue, M.; Takamatsu, K.; Tachibana, K. J. Org. Chem. 1999, 64, 9399.
8. Fernandez-Megia, E.; Gourlaouen, N.; Ley, S. V.; Rowlands, G. J. Synlett 1998, 991.
9. Horita, K.; Nishikawa, T.; Isobe, M. Tetrahedron 1998, 54, 6639.
10. Chiba, N.; Takeoka, J.; Ando, K.; Tsutsumi, N.; Ogawa, S. Tetrahedron 1997, 53, 16287.
11. Shimura, T.; Komatsu, C.; Matsumura, M.; Shimada, Y.; Ohta, K.; Mitsunobu, O. Tetrahedron Lett. 1997, 38, 8341.
12. Sin, N.; Kallmerten, J. Tetrahedron Lett. 1996, 37, 5645.
13. Sasaki, M.; Inoue, M.; Tachibana, K. J. Org. Chem. 1994, 59, 715.
14. Alonso, R. A.; Burgey, C. S.; Rao, B. V.; Vite, G. D.; Vollerthun, R.; Zottola, M. A.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 6666.
15. Hang, H. C.; Bertozzi, C. R. J. Am. Chem. Soc. 2001, 123, 1242.
16. Jackman, J. E.; Fierke, C. A.; Tumey, L. N.; Pirrung, M.; Uchiyama, T.; Tahir, S. H.; Hindsgaul, O.; Raetz, C. R. H. J. Biol. Chem. 2000, 275, 11002.
17. Li, X.; Uchiyama, T.; Raetz, C. R. H.; Hindgaul, O. Org. Lett. 2003, 5, 539.
18. For some organometallic approaches fromglycals, see: Fernández, E.; Ruiz, A.; Claver, C.; Castillo'n, S.; Polo, A.; Piniella, J. F.; Alvarez-Larena, A. Organometallics 1998, 17, 2857.
19. Linker, T.; Sommermann, T.; Kahlenberg, F. J. Am. Chem. Soc. 1997, 119, 9377.
20. Cousins, G. S.; Hoberg, J. O. Chem. Soc. Rev . 2000, 29, 165.
21. Lebel, H.; Marcoux, J.-F.; Malinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
22. Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.
23. Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919.
24. Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
25. For recent innovations on the synthesis of 2-C-branched sugars involving 1,2-cyclopropanation of glycal followed by ring opening, see: (a) Beyer, J.; Madsen, R. J. Am. Chem. Soc. 1998, 120, 12137.
26. Beyer, J.; Skaanderup, P. R.; Madsen, R. J. Am. Chem. Soc. 2000, 122, 9575.
27. Shao, H.; Ekthawatchair, S.; Wu, S.-H.; Zou, W. Org. Lett. 2004, 6, 3497.
28. Tian, Q.; Dong, L.; Ma, X.; Xu, L.; Hu, C.; Zou, W.; Shao, H. J. Org. Chem. 2011, 76, 1045.
29. Sridhar, R. R.; Ashalu, K. C. Chandrasekaran, S. Org. Lett. 2004, 6, 1777.
30. Ramana, C. V.; Murall, R.; Nagarajan, M. J. Org. Chem. 1997, 62, 7694.
31. Oh, J.; Lee, C. R.; Chun, K. H. Tetrahedron Lett. 2001, 427, 4879.
32. Dahl, R. S.; Finney, N. S. J. Am. Chem. Soc. 2004, 126, 8356.
33. For similar ring-opening reaction of six-membered semicyclicN, O-acetals, see: Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 12510.
34. Li, G.; Kaplan, M. J.; Wojtas, L.; Antilla, J. C. Org. Lett. 2010, 12, 1960.
35. Cakir, S. P.; Mead, K. T. Synthesis 2008, 871.
36. For synthesis of N-acyl-O-alkylacetals, see: Katritzky, A. R.; Pernak, J.; Fan, W.-Q.; Saczewski, F. J. Org. Chem. 1991, 56, 4439.
37. Cai, Y.; Ling, C.-C.; Bundle,D.R. Org. Lett. 2005, 7, 4021.
38. The anti-8 isomer refers to the configuation of the substituents at the 2 and 6 positions of the pyran ring.
39. For related reference on the sterochemistry assignment, see: Jiménez, O.; Rosa, G.; Lavillar, R. Angew. Chem., Int. Ed. 2005, 44, 6521.