Borane/Bu2BOTf: A mild reagent for the regioselective reductive ring opening of benzylidene acetals in carbohydrates

Tetrahedron Letters

Volumn 39, Issue 5-6, 1998, Pages 355-358

  Jiang, Lu ^a   Chan, Tak Hang ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032576812     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10599-8     Document Type: Article

References (11)

1. 1. (a) Bhattacharjee, S. S.; Gorin, P. A. Can. J. Chem. 1969, 47, 1195;
2. (b) Liptak, A.; Imre, J.; Harangi, J.; Nanasi, P. Tetrahedron 1982, 38, 3721;
3. (c) Gejas, J. Adv. Carbohydr. Chem. Biochem. 1981, 39, 71;
4. (d) Garegg, P. J. Pure App. Chem. 1984, 56, 845;
5. (e) Johansson, R.; Samuelsson, B. J. Chem. Soc., Perkin Trans. 1 1984, 2371.
6. 2. Garegg, P. J.; Hultberg, H.; Wallin, S. Carbohydr. Res. 1982, 108, 97.
7. 3. DeNinno, M. P.; Etienne, J. B.; Duplantier, K. C. Tetrahedron Lett. 1995, 36, 669.
8. 4. Ek, M.; Garegg, P. J.; Hultberg, H.; Oscarson, S. J. Carbohydr. Chem. 1983, 2, 305.
9. 5. Okawa, M.; Liu, W. C.; Nakai, Y.; Koshida, S.; Fukase, K.; Kusumoto, S. Synlett. 1996, 1179.
10. 6. Benzylidene and isopropylidene acetals were prepared according to the procedures described in: Ferro, V.; Mocerino, M.; Stick, R. V.; Tilbrook, M. G. Aust. J. Chem. 1988, 41, 813.
11. 3 in THF was used for every mmol of the substrate. For larger reaction scale (e.g. 10 mmol), the amount of borane required can be reduced to three fold excess.