SYNTHESIS AND PROPERTIES OF SOME STEREOISOMERIC LONG-CHAIN 1,2,3,4-TETROLS

Article abstract of DOI:10.1016/S0040-4020(01)87363-4

Syntheses of 1,2S,3R,4R, 1,2S,3R,4S, 1,2R,3S,4R, and 1,2S,3S,4R-icosanetetrol, as well as of 1,2S,3S,4R-octadecanetetrol, are described, all based upon Wittig reactions of 1,2,3-protected pentodialdo-1,4-furanoses, serving as "chiral templates", with pentadecyl (or tridecyl) triphenylphosphorane, followed by catalytic hydrogenation, hydrolysis, and reduction.The tetrols, all forming liquid crystals on heating, are characterized spectroscopically and as their O-tetraacetates.The latter serve admirably for GLC-separation and -characterization of all non-enantiomeric tetrols.From the sign of rotation and GLC-comparison with the synthetic O-tetraacetates it follows that the 1,2,3,4-octadecanetetrol and 1,2,3,4-icosanetetrol, reported several years ago as the predominant members of a homologous series of tetrols derived from the gum-resin of Commiphora mukul, possess the 2S,3S,4R-configuration ("D-xylo").