Chemistry of 1-alkoxy-1-glycosyl radicals: The manno- and rhamnopyranosyl series. Inversion of α- to β-pyranosides and the fragmentation of anomeric radicals

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 605-615

  Crich, David ^a   Sun, Sanxing ^a   Brunckova, Jarmila ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS; TECHNIQUE;

EID: 0030027050     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951194h     Document Type: Article

References (148)

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100. 1,4-Hydrogen atom abstraction reactions: (a) Brunton, G.; Griller, D.; Barclay, L. R C.; Ingold, K. U. J. Am. Chem Soc. 1976, 98, 6803. (b) Wallace, T. J.; Gritter, R. J J. Org. Chem. 1961, 26, 5256. (c) Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085.
101. 1,4-Hydrogen atom abstraction reactions: (a) Brunton, G.; Griller, D.; Barclay, L. R C.; Ingold, K. U. J. Am. Chem Soc. 1976, 98, 6803. (b) Wallace, T. J.; Gritter, R. J J. Org. Chem. 1961, 26, 5256. (c) Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085.
102. 1,4-Hydrogen atom abstraction reactions: (a) Brunton, G.; Griller, D.; Barclay, L. R C.; Ingold, K. U. J. Am. Chem Soc. 1976, 98, 6803. (b) Wallace, T. J.; Gritter, R. J J. Org. Chem. 1961, 26, 5256. (c) Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085.
103. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
104. The quenching stereoselectivity of such radicals must be a function of the trap employed, of the radical conformation, and of any C-2 substituent. The methyl 2-deoxy-α-glucopyranos-2-yl radical adds to activated alkenes with good selectivity from the equatorial site, but related C-2 substituted radicals are trapped with moderate selectivity along the axial direction by both oxygen and tributyltin deuteride. (a) Giese, B.; Groninger, K. Tetrahedron Lett. 1984, 25, 2743. (b) Moutel, S.; Prandi, J. Tetrahedron Lett. 1994, 35, 8163. (c) Horton, D.; Priebe, W.; Sznaidman, M. L. J. Org. Chem. 1993, 58, 1821.
105. The quenching stereoselectivity of such radicals must be a function of the trap employed, of the radical conformation, and of any C-2 substituent. The methyl 2-deoxy-α-glucopyranos-2-yl radical adds to activated alkenes with good selectivity from the equatorial site, but related C-2 substituted radicals are trapped with moderate selectivity along the axial direction by both oxygen and tributyltin deuteride. (a) Giese, B.; Groninger, K. Tetrahedron Lett. 1984, 25, 2743. (b) Moutel, S.; Prandi, J. Tetrahedron Lett. 1994, 35, 8163. (c) Horton, D.; Priebe, W.; Sznaidman, M. L. J. Org. Chem. 1993, 58, 1821.
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109. 22
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