Synthesis of 1,2:4,5-Di-O-isopropylidene-D-erythro-2,3- hexodiulo-2,6-pyranose. A highly enantioselective ketone catalyst for epoxidation [[β-D-erythro-2,3-Hexodiulo-2,6-pyranose, 1,2:4,5-bis-O-(1-methylethylidene)-]]

Organic Syntheses

Volumn 80, Issue , 2003, Pages 1-8

  Tu, Yong ^a   Frohn, Michael ^a   Wang, Zhi Xian ^a   Shi, Yian ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85026859587     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.080.0001     Document Type: Article

References (43)

1. McDonald, E. J. Carbohydr. Res. 1967, 5, 106
2. James, K.; Tatchell, A. R.; Ray, P. K. J. Chem. Soc. C 1967, 2681
3. Brady, R. F., Jr. Carbohydr. Res. 1970, 15, 35
4. Tipson, R. S.; Brady, R. F. Jr.; West, B. F. Carbohydr. Res. 1971, 16, 383
5. Prisbe, E. J.; Smejkal, J.; Verheyden, J. P. H.; Moffatt, J. G. J. Org. Chem., 1976, 41, 1836
6. Fayet, C.; Gelas, J. Carbohydr. Res. 1986, 155, 99
7. Maryanoff, B. E.; Reitz, A. B.; Nortey, S. O. Tetrahedron 1988, 44, 3093
8. Mio, S.; Kumagawa, Y.; Sugai, S. Tetrahedron 1991, 47, 2133
9. Kang, J.; Lim, G. J.; Yoon, S. K.; Kim, M. Y. J. Org. Chem. 1995, 60, 564
10. Fung, W.-H.; Yu, W.-Y.; Che, C.-M. J. Org. Chem. 1998, 63, 2873.
11. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205
12. Murray, R. W. Chem. Rev. 1989, 89, 1187
13. Curci, R.; Dinoi, A.; Rubino, M. F. Pure & Appl. Chem. 1995, 67, 811
14. Clennan, E. L. Trends Org. Chem. 1995, 5, 231
15. Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581
16. Denmark, S. E.; Wu, Z. Synlett 1999, 847.
17. Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155
18. Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831
19. Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391
20. Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587
21. Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491
22. Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311
23. Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921
24. Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995
25. Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288
26. Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622
27. Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621
28. Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943
29. Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659
30. Adam, W.; Saha-Möller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749
31. Wang, Z.-X.; Miller, S. M.; Anderson, O. P.; Shi, Y. J. Org. Chem. 1999, 64, 6443.
32. Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806
33. Wang, Z.-X.; Tu, Y.; Frohn, M.; Shi, Y. J. Org. Chem. 1997, 62, 2328
34. Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224
35. Frohn, M.; Dalkiewicz, M.; Tu, Y.; Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 2948
36. Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 3099
37. Cao, G.-A.; Wang, Z.-X.; Tu, Y.; Shi, Y. Tetrahedron Lett. 1998, 39, 4425
38. Zhu, Y.; Tu, Y.; Yu, H.; Shi, Y. Tetrahedron Lett. 1998, 39, 7819
39. Tu, Y.; Wang, Z.-X.; Frohn, M.; He, M.; Yu, H.; Tang, Y.; Shi, Y. J. Org. Chem. 1998, 63, 8475
40. Wang, Z.-X.; Cao, G.-A.; Shi, Y. J. Org. Chem. 1999, 64, 7646
41. Warren, J. D.; Shi, Y. J. Org. Chem. 1999, 64, 7675
42. Shu, L.; Shi, Y. Tetrahedron Lett. 1999, 40, 8721.
43. Chen, C.-C.; Whistler, R. L. Carbohydr. Res. 1988, 175, 265.