TY - JOUR
T1 - From secondary alcohols to tertiary fluoro substituents: A simple route to hydroxymethyl branched sugars with a fluorine substituent at the branching point
AU - Schalli, Michael
AU - Thonhofer, Martin
AU - Wolfsgruber, Andreas
AU - Weber, Hansjörg
AU - Fischer, Roland
AU - Saf, Robert
AU - Stütz, Arnold
PY - 2016
Y1 - 2016
N2 - 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.
AB - 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.
U2 - 10.1016/j.carres.2016.10.013
DO - 10.1016/j.carres.2016.10.013
M3 - Article
SN - 0008-6215
VL - 436
SP - 11
EP - 19
JO - Carbohydrate Research
JF - Carbohydrate Research
ER -