Titanium(III)-promoted stereoselective synthesis of simple C-glycosides

Journal of Organic Chemistry

Volumn 62, Issue 13, 1997, Pages 4204-4205

  Spencer, Roxanne P ^a   Schwartz, Jeffrey ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; TITANIUM;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030795023     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9702352     Document Type: Article

References (37)

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7. 12, see: (h) Abrecht, S.; Scheffold, R. Chimia 1985, 35, 211-212. For electrochemical generation of the anomeric radical, see: (i) Rondinini, S.; Mussini, P. R.; Ferzetti, V.; Monti, D. Electrochim. Acta 1991, 36, 1095-1098.
8. 12, see: (h) Abrecht, S.; Scheffold, R. Chimia 1985, 35, 211-212. For electrochemical generation of the anomeric radical, see: (i) Rondinini, S.; Mussini, P. R.; Ferzetti, V.; Monti, D. Electrochim. Acta 1991, 36, 1095-1098.
9. 12, see: (h) Abrecht, S.; Scheffold, R. Chimia 1985, 35, 211-212. For electrochemical generation of the anomeric radical, see: (i) Rondinini, S.; Mussini, P. R.; Ferzetti, V.; Monti, D. Electrochim. Acta 1991, 36, 1095-1098.
10. 12, see: (h) Abrecht, S.; Scheffold, R. Chimia 1985, 35, 211-212. For electrochemical generation of the anomeric radical, see: (i) Rondinini, S.; Mussini, P. R.; Ferzetti, V.; Monti, D. Electrochim. Acta 1991, 36, 1095-1098.
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17. 2 at -40 °C.
18. 1b
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20. 8, no deuterium incorporation was detected by NMR.
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30. Carbohydrate radicals can undergo a 1,5-hydrogen atom shift; this route has been used for epimerization of the C-5 center in glucopyranosides (see: De Mesmacker, A.; Waldner, A.; Hoffmann, P.; Winkler, T. Synlett 1994, 330-332 and references therein). This radical is reduced to the stable, coupled product in the presence of tin hydride.
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35. 2TiCl-enolates, see: Veya, P.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 4892-4898. Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc. 1983, 105, 1664-1665.
36. 2TiCl-enolates, see: Veya, P.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 4892-4898. Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc. 1983, 105, 1664-1665.
37. 2TiCl-enolates, see: Veya, P.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 4892-4898. Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037-2040. Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc. 1983, 105, 1664-1665.