Efficient "dehomologation" of di-O-isopropylidenehexofuranose derivatives to give O-isopropylidenepentofuranoses by sequential treatment with periodic acid in ethyl acetate and sodium borohydride

Journal of Organic Chemistry

Volumn 61, Issue 15, 1996, Pages 5178-5179

  Xie, Meiqiang ^a   Berges, David A ^a   Robins, Morris J ^a  

^a Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030036748     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960355u     Document Type: Article

References (18)

1. Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163.
2. Hall, N. Science 1994, 266, 32-34.
3. (a) Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 3586-3588.
4. (b) Li, Y.-L.; Sun, X.-L.; Wu, Y.-L. Tetrahedron 1994, 50, 10727-10738.
5. Robins, M. J.; Samano, V.; Johnson, M. D. J. Org. Chem. 1990, 55, 410-412.
6. Lee, K.; Wiemer, D. F. J. Org. Chem. 1993, 58, 7808-7812.
7. Rosenthal, A.; Nguyen, L. J. Org. Chem. 1969, 34, 1029-1034.
8. Lourens, G. J.; Koekemoer, J. M. Tetrahedron Lett. 1975, 3719-3722.
9. Garegg, P. J.; Samuelsson, B. Carbohydr. Res. 1978, 67, 267-270.
10. (a) Tronchet, J. M. J.; Gentile, B. Carbohydr. Res. 1975, 44, 23-35.
11. (b) Tadano, K.; Idogaki, Y.; Yamada, H.; Suami, T. J. Org. Chem. 1987, 52, 1201-1210.
12. Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326.
13. (a) Hasegawa, A.; Kiso, M. Carbohydr. Res. 1980, 79, 265-270.
14. (b) Uryu, T.; Koyama, Y.; Matsuzaki, K. J. Polym. Sci., Polym. Lett. Ed. 1979, 17, 673-678.
15. Tsutsumi, H.; Kawai, Y.; Ishido, Y. Carbohydr. Res. 1979, 73, 293-296.
16. Barbat, J.; Gelas, J.; Horton, D. Carbohydr. Res. 1991, 219, 115-121.
17. Varela, O.; Zunszain, P. A. J. Org. Chem. 1993, 58, 7860-7864.
18. Robins, M. J.; Mengel, R.; Jones, R. A.; Fouron, Y. J. Am. Chem. Soc. 1976, 98, 8204-8213.