From secondary alcohols to tertiary fluoro substituents: A simple route to hydroxymethyl branched sugars with a fluorine substituent at the branching point.
From a secondary hydroxyl group, by the simple sequence of oxidation, Wittig reaction of the obtained ulose with methoxymethylene triphenyl phosphorane, exposure of the resulting exocyclic enol ether to Selectfluor and subsequent reduction of the α-fluoro aldehyde thus obtained, tertiary fluoro substituents can be introduced into carbohydrate and carbohydrate-related scaffolds at a branching point now bearing a new hydroxymethyl group.
Glycogroup, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria.
Michael
M
Schalli
Glycogroup, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria.
Martin
M
Thonhofer
Glycogroup, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria.
Andreas
A
Wolfsgruber
Institute for Organic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria.
Hansjörg
H
Weber
Institute for Inorganic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria.
Roland
R
Fischer
Institute for Chemistry and Technology of Materials, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria.
Robert
R
Saf
Glycogroup, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria. Electronic address: stuetz@tugraz.at.
Arnold E
AE
Stütz
D000438:Alcohols / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000438:Alcohols; D002241:Carbohydrates; D005461:Fluorine; D005459:Fluorides
Branched-chain fluorosugar; Electrophilic fluorination; Selectfluor; Synthesis