Stereoselective sulfoxidation of α-mannopyranosyl thioglycosides: The exo-anomeric effect in action

Chemical Communications

Volumn , Issue 24, 1998, Pages 2763-2764

  Crich, David ^a   Mataka, Jan ^a   Sun, Sanxing ^a   Lam, K C ^b   Rheingold, Arnold L ^b   Wink, Donald J ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SULFOXIDE; THIOGLYCOSIDE;

ARTICLE; OXIDATION; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0032556806     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804126a     Document Type: Article

References (17)

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5. However, we note that the two unprotected β-galactosyl phenyl sulfoxides are hydrolyzed at different rates by aqueous TfOH, presumably due to differential intramolecular hydrogen bonding interactions: N. Khiar, I. Alonso, N. Rodriguez, A. Fernandez-Mayorales, J. Jimenez-Barbero, O. Nieto, F. Cano, C. Foces-Foces and M. Martin-Lomas, Tetrahedron Lett., 1997, 38, 8267.
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12. A further, unassigned example of diastereoselective sulfoxidation of an α-mannosyl thioglycoside: G. Stork and J. J. La Clair, J. Am. Chem. Soc., 1996, 118, 247.
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17. 2 with 1551 having I > 2σ(I). Final agreement factors for 199 least-squares parameters (with values for all independent reflections in parentheses): R = 0.0864 (0.1039), wR2 = 0.2847 (0.2582), GOF = 2.415 (2.414). CCDC 182/1088. The crystallographic data is available as a .cif file: see http://www.rsc.org/suppdata/cc/ 1998/2763/