Anders Kjer, D. Kjer, T. Skrydstrup
1986
Citations
0
Influential Citations
20
Citations
Journal
Tetrahedron
Abstract
Abstract Syntheses of 1, 2 S , 3 R , 4 R , 1, 2 S , 3 R , 4 S , 1, 2 R , 3 S , 4 R , and 1, 2 S , 3 S , 4 R - icosanetetrol, as well as of 1, 2 S , 3 S , 4 R -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) triphenyIphosphorane, 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 2 S , 3 S , 4 R - configuratlon (‘D-xylo’).