Mv. Anikin et al., A CONVENIENT APPROACH TO SYNTHESIS OF THI OGLYCOSIDE-TYPE ANALOGS OF GALACTOSYLDIGLYCERIDES, Bioorganiceskaa himia, 19(11), 1993, pp. 1102-1110
A useful semiproduct for preparing thioglycoside-type analogues of gal
actosyldiglycerides, traacetyl-beta-D-galactopyranosyl)-3-thioglycerol
, has been synthesized by glycosylation of 3-thioglycerol with beta-ac
etylgalactosyl bromide. Its acylation with palmitoyl chloride gave etr
aacetyl-beta-D-galactopyranosyl)-3-thioglycerol as a mixture of two di
astereomers separated by flow recycling HPLC on a silica gel column. T
he final removal of the protective acetyl groups led to oyl-S-(beta-D-
galactopyranosyl)-1-thio-sn-glycerol and yl-S-(beta-D-galactopyranosyl
)-3-thio-sn-glycerol.