β-selective C-glycosidations: Lewis-acid mediated reactions of carbohydrates with silyl ketene acetals

Tetrahedron Letters

Volumn 38, Issue 39, 1997, Pages 6815-6818

  Minehan, Thomas G ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; GLYCOSIDE; PORPHYRIN DERIVATIVE; TOLYPORPHIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030796701     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01602-X     Document Type: Article

References (14)

1. Minehan, T. G.; Kishi, Y. preceding paper.
2. For a recent review on C-glycosides in general, see: Levy, D. E.; Tang, C. The Chemistry of C-Glycosides, Pergamon Press, Tarrytown, 1995.
3. For a recent review on C-glycoside synthesis in general, see: Postema, M. H. D. C-Glycoside Synthesis, CRC Press, Inc., Boca Raton, FL, 1995.
4. Lewis, M. D.; Cha, K; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. The examples shown below are representative in the terms of the efficiency and stereoselectivity of bond formation. (formula presented)
5. (a) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289.
6. (b) Kozikowski, A. P.; Sorgi, K. L. Tetrahedron Lett. 1982, 23, 2281.
7. (c) Schmidt, R. R.; Hoffman, M. Tetrahedron Lett. 1982, 23, 409.
8. (d) Hosomi, A; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383.
9. β-Selective C-allylation of carbohydrates bearing a C.2 phthalimido group is known: (a) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160.
10. (b) Roe, B. A.; Boojamra, C. G.; Griggs, J. L.; Bertozzi, C. R. J. Org. Chem. 1996, 61, 6442.
11. Nicolaou, K. C.; McGarry, D. G.; Somers, P. K.; Veale, C. A.; Furst, G. T. J. Am. Chem. Soc. 1987, 109, 2504.
12. For a recent example of β-selective C-glycosidation by silyl ketene acetals, see: Smoliakova, I. P.; Caple, R.; Gregory, D.; Smit, W. A.; Shashkov, A. S.; Chizhov, O. S. J. Org. Chem. 1995, 60, 1221.
13. Attempted C-allylation of S-1 and S-2 with γ,γ-dimethylallytrimethyIsilane gave a complex mixture of products, containing only minor amounts of the desired products.
14. 4 (0.leq.); 55% yield.