Environmentally benign aryl C-glycosidations of unprotected sugars using montmorillonite K-10 as a solid acid

Tetrahedron Letters

Volumn 38, Issue 42, 1997, Pages 7375-7378

  Toshima, Kazunobu ^a   Ushiki, Yasunobu ^a   Matsuo, Goh ^a   Matsumura, Shuichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; GLYCOSYLATION; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030848451     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01724-3     Document Type: Article

References (16)

1. Rohr, J. ; Thiericke, R. Nat. Prod. Rep. 1992, 103.
2. Hansen, M. R.; Hurley, L. H. Acc. Chem. Res. 1996, 29, 249.
3. (a) Postema, M. H. D. Tetrahedron 1992, 40, 8545;
4. (b) Levy, D. E.; Tang, C. In The Chemistry of C-Glycosides, Pergamon Press, Oxford, 1995.
5. (a) Balogh, M. In Organic Chemistry Using Clays, Springer-Verlag, New York, 1993;
6. (b) Izumi, K.; Urabe, K.; Onaka, M. In Zeolite, Clay, and Heteropoly Acid in Organic Reactions, VCH, Weinheim, 1992, ch. 1, p. 21.
7. For a use of montmorillonite K-10 as a glycosidation reagent, see: (a) Florent, J.-C; Monneret, C. J. Chem. Soc., Chem. Commun. 1987, 1171;
8. (b) Fukase, K.; Winarno, H.; Kusumoto, S. Chem. Express 1993, 8, 409;
9. (c) Toshima, K.; Ishizuka, T.; Matsuo, G.; Nakata, M. Synlett 1995, 306;
10. (d) Toshima, K.; Miyamoto, N.; Matsuo, G.; Nakata, M.; Matsumura, S. Chem. Commun. 1996, 1379.
11. For a use of unprotected sugar in aryl C-glycosidation, see: (a) Toshima, K.; Matsuo, G.; Ishizuka, T.; Nakata, M.; Kinoshita, M. J. Chem. Soc., Chem. Commun. 1992, 1641;
12. (b) Toshima, K.; Matsuo, G.; Nakata, M. J. Chem. Soc., Chem. Commun. 1994, 997.
13. 5 and distillation.
14. Isolated yields after purification by column chromatography.
15. 1H NMR spectroscopy (270 MHz).
16. All aryl C-glycosides were purified by silica-gel column chromatography and were fully characterized by spectroscopic means.