Iodomethyl group as a hydroxymethyl synthetic equivalent: application to the syntheses of D-manno-hept-2-ulose and l-fructose derivatives.
The one-carbon elongation of aldoses to ketoses using iodomethyllithium as the key reagent in the homologation step is exemplified by the preparation of two carbohydrates of chemical and biological interests: d-manno-hept-2-ulose from d-mannose and l-fructose from l-arabinose.
Université Joseph Fourier, UMR CNRS 5616, Chimie Recherche (LEDSS), BP 53, 38041 Grenoble Cedex 9, France.
Bernard
B
Bessières
Christophe
C
Morin
D002384:Catalysis; D005632:Fructose / Q000138:chemical synthesis*; D006539:Heptoses / Q000138:chemical synthesis*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D007202:Indicators and Reagents; D007661:Ketoses / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D008358:Mannose / Q000138:chemical synthesis*; D008697:Methane / Q000737:chemistry; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D010429:Pentoses / Q000737:chemistry; D013237:Stereoisomerism
D006539:Heptoses; D006847:Hydrocarbons, Iodinated; D007202:Indicators and Reagents; D007661:Ketoses; D009005:Monosaccharides; D010429:Pentoses; D005632:Fructose; D008094:Lithium; D008697:Methane; D008358:Mannose