Substitution and remote protecting group influence on the oxidation/addition of alpha-substituted 1,2-anhydroglycosides: a novel entry into C-ketosides.
[reaction: see text] C-Ketosides are valuable intermediates in chemical synthesis and as glycoside mimics. This manuscript describes the efficient generation of these substrates from alpha-alkyl-substituted glycals and an oxidative, C-C bond-forming sequence where the choice of C(3) protecting group was critical.
Roberts
Scott W
SW
Department of Chemistry, University of Utah, 315 S 1400 E, Salt Lake City, Utah 84112, USA.
Rainier
Jon D
JD
D002384:Catalysis; D006027:Glycosides / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction
D006027:Glycosides; D007202:Indicators and Reagents; D017646:Organosilicon Compounds