An efficient synthesis of β-C-glycosides based on the conformational restriction strategy: Lewis acid promoted silane reduction of the anomeric position with complete stereoselectivity

Organic Letters

Volumn 6, Issue 21, 2004, Pages 3751-3754

  Terauchi, Masaru ^a   Abe, Hiroshi ^a   Matsuda, Akira ^a   Shuto, Satoshi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; LEWIS ACID; SILANE DERIVATIVE;

ARTICLE; CYCLIZATION; REDUCTION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

ACIDS; CARBOHYDRATE CONFORMATION; GLYCOSIDES; SILANES; STEREOISOMERISM;

EID: 7044247778     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048525+     Document Type: Article

References (39)

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21. Examples of β-C-glycoside synthesis by Kishi's Lewis acid prompted silane reduction; see: (a) Lancelin, J.-M.; Zollo, P. H. A.; Sinay, P. Tetrahedron Lett. 1983, 24, 4833-4836. (b) Kraus, G. A.; Molina, M. T. J. Org. Chem. 1988, 53, 752-753. (c) Czernecki, S.; Ville, G. J. Org. Chem. 1989, 54, 610-612. (d) Dondoni, A.; Marra, A.; Scherrmann, M.-C. Tetrahedron Lett. 1993, 34, 7323-7326. (e) Xie, J.; Durrat, F.; Valéry, J.-M. J. Org. Chem. 2003, 68, 7896-7898.
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31. In the transition state of nucleophilic addition reactions to carbonyls, the energy of the transition state can be lowered by hyperconjugation between an antiperiplanar vicinal σ-bond to the antibonding component (σ*‡) of the newly forming bond; see: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Cieplak, A. S.; Tait, B. D.; Johnson, C. R. J. Am. Chem. Soc. 1989, 111, 8447-8462. (c) Cieplak, A. S. Chem. Rev. 1999, 99, 1265-1336.
32. In the transition state of nucleophilic addition reactions to carbonyls, the energy of the transition state can be lowered by hyperconjugation between an antiperiplanar vicinal σ-bond to the antibonding component (σ*‡) of the newly forming bond; see: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Cieplak, A. S.; Tait, B. D.; Johnson, C. R. J. Am. Chem. Soc. 1989, 111, 8447-8462. (c) Cieplak, A. S. Chem. Rev. 1999, 99, 1265-1336.
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38. 2 was used as the Lewis acid, the 3,4-cyclic ketal moiety of the conformationally restricted substrates was partially reduced.
39. 1,2 values for the C-glucosides or by NOE experiments for the C-mannosides.