Regioselective Reductive Opening of 4,6-O-Benzylidene Acetals of Glucose or Glucosamine Derivatives by BH3·Me2NH - BF3-OEt2

Synlett

Volumn 1996, Issue 12, 1996, Pages 1179-1180

  Oikawa, Masato ^a   Liu, Wen Chi ^a   Nakai, Yoshihiko ^a   Koshida, Shuhei ^a   Fukase, Koichi ^a   Kusumoto, Shoichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003007599     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5724     Document Type: Article

References (11)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley and Sons, Inc.: New York, 1991.
2. Garegg, P. J.; Hultberg, H.; Wallin, S. Carbohydr. Res. 1982, 108, 97-101.
3. DeNinno, M. P.; Etienne, J. B.; Duplantier, K. C. Tetrahedron Lett. 1995, 36, 669-672.
4. Johansson, R.; Samuelsson, B. J. Chem. Soc., Perkin Trans. 1 1984, 2371-2374.
5. Guindon, Y.; Girard, Y.; Berthiaume, S.; Gorys, V.; Lemieux, R.; Yoakim, C. Can. J. Chem. 1990, 68, 897-902.
6. Mikami, T.; Asano, H.; Mitsunobu, O. Chem. Lett. 1987, 2033-2036.
7. Fügedi, P.; Lipták, A.; Nánási, P.; Szejtli, J. Carbohydr. Res. 1982, 104, 55-67.
8. Oikawa, M.; Liu, W.-C.; Wada, A. Yoshizaki, H.; Fukase, K.; Suda, Y.; Kusumoto, S. submitted to Bull. Chem. Soc. Jpn.
9. 3 has been reported, see: Ek, M.; Garegg, P. J.; Hultberg, H.; Oscarson, S. J. Carbohydr. Chem. 1983, 2, 305-311.
10. The reaction was not completed at 0 °C.
11. 3N - HCOOH for reduction of a pyrazine ring has been reported, see: Forsch, R. A.; Rosowsky, A. J. Org. Chem. 1985, 50, 2582-2583.