NOUVELLE VOIE D'ACCES STEREOSELECTIVE AUX ESTERS ACRYLIQUES SON APPLICATION EN CHIMIE DES SUCRES

Article abstract of DOI:10.1016/0008-6215(85)85194-6

Regio- and stereo-selective synthesis of an acryl residue by treatment of an allyl alcohol with (Z,E)-1-fluoro-1-methoxy-2-phenylsulfinylpropene was performed in three consecutive reactions in the same flask; displacement of F^- by the alcohol, Claisen rearrengement, and dehydrosulfinylation.Thus, 1,5-anhydro-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-enitol gave methyl 3,7-anhydro-6,8-benzylidene-2,4,5-trideoxy-2-C-methylene-D-ribo-oct-4-enonate and methyl 2-O-allyl-4,6-dideoxy-α-D-erythro-hex-4-enopyranoside gave methyl (methyl 2-O-allyl-3,4,6-trideoxy-5-C-methyl-6-C-methylene-α-L-threo-hept-3-enopyranosyd)uronate, which has a chiral quaternary C-5 atom.