A new bismuth nitrate-induced stereospecific glycosylation of alcohols

Heterocycles

Volumn 61, Issue , 2003, Pages 101-104

  Banik, Bimal K ^a   Adler, Dorothy ^a   Nguyen, Phuong ^a   Srivastava, Neeta ^a  

^a UNIVERSITY OF TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BISMUTH NITRATE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GLYCOSYLATION; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

EID: 0346392169     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-s63     Document Type: Article

References (14)

1. For a review on O-glycosylation, see: K. Toshima and K. Tatsuta, Chem. Rev., 1993, 93, 1503.
2. For example of glycosylation, see: R. R. Schmidt, Angew. Chem., 1986, 98, 213.
3. R. J. Ferrier, Adv. Carbohydr. Chem. Biochem., 1969, 199.
4. (a) G. Descotes and J. C. Martin, Carbohydr. Res., 1979, 68, 33.
5. (b) P. Bhate, D. Horton, and W. Priebe, Carbohydr. Res., 1985, 144, 331.
6. For an example, see: K. Toshima, T. Ishizuka, G. Matsuo, and M. Nakata, Synlett, 1995, 306.
7. For a recent example towards α-anomer, see: B. K. Banik, M. S. Manhas, and A. K. Bose, J. Org. Chem., 1994, 59, 4714.
8. For a recent example towards β-anomer, see: B. Yu and Z. Yang, Tetrahedron Lett., 2000, 41, 2961.
9. For a recent example, see: B. K. Banik and F. F. Becker, Bioorg. & Med. Chem., 2001, 9, 593 and references cited therein.
10. I. Banik, F. F. Becker, and B. K. Banik, J. Med. Chem., 2003, 46, 12 and references cited therein.
11. B. K. Banik, S. Samajdar, I. Banik, O. Zegrocka, and F. F. Becker, Heterocycles, 2001, 55, 227.
12. S. Samajdar, F. F. Becker, and B. K. Banik, Tetrahedron Lett., 2000, 41, 8017.
13. N. Srivastava and B. K. Banik, J. Org. Chem., 2003, 68, 2109.
14. A representative procedure: A mixture of methanol (1 mL), glycal (1.5 mmol), bismuth nitrate pentahydrate (0.2 mmol) was stirred at room temperature for overnight. The progress of the reaction was monitored by TLC. After the reaction, dichloromethane (20 mL) was added to it and then it was washed with saturated sodium bicarbonate (5 mL), brine (5 mL) and dried with sodium sulfate. The solvent was evaporated in vacuo and directly subjected to column chromatography using silica gel (230-400 mesh, 20% ethyl acetate-80% hexane) to afford the pure product. The reaction was performed with 1 mmol of alcohols and THF was used as the reaction media in Entries 3, 4 and 6.