Acetolysis of 2,4-O-benzylidene-L-ribo-hex-5-enitol derivative

Article abstract of DOI:10.1016/0008-6215(94)80036-7

Acetolysis of (Z)-1,3-di-O-acetyl-2,4-O-benzylidene-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-L-ribo-hex-5-enitol afforded, besides 2-C-<(S)-acetoxy(2,4-dichlorophenyl)methyl>-3,4,6-tri-O-acetyl-2-deoxy-β-D-allo- and -gluco-hexopyranosylbenzene, (E)-1,2,3,4-tetra-O-acetyl-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-lyxo- and -L-ribo-hex-5-enitol as main products.The rate of this reaction as well as the ratio of the products depends on the chirality of C-3.This was confirmed by acetolysis of the corresponding L-erythro-pent-4-enitol derivative.