Synthesis of alpha-CF2-mannosides and their conversion to fluorinated pseudoglycopeptides.
A methodology allowing the synthesis alpha-CF(2)-mannosides, based on the addition of a difluoroenoxysilane to a glycal followed by a dihydroxylation reaction, is described. The resulting 2,2-difluoro-2-mannosylacetate is converted into two pseudoglycopeptides which may act as E- and P-selectin inhibitors.
Poulain
Florent
F
Université et INSA de Rouen, CNRS, UMR 6014 C.O.B.R.A.-IRCOF, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex, France.
Serre
Anne-Lise
AL
Lalot
Jérôme
J
Leclerc
Eric
E
Quirion
Jean-Charles
JC
D040761:Biomimetic Materials / Q000138:chemical synthesis; D006020:Glycopeptides / Q000138:chemical synthesis*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry; D008362:Mannosides / Q000138:chemical synthesis* / Q000737:chemistry
D006020:Glycopeptides; D006845:Hydrocarbons, Fluorinated; D008362:Mannosides