105368-53-4

Upstream product

• 105265-43-8 5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20-hexadecadeoxy-L-lyxo-icosofuranose 
• 1944-80-5 pentadecyltriphenylphosphonium bromide 
• 105368-49-8 methyl (Z)-5,6-dehydro-5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20-hexadecadeoxy-2,3-O-isopropylidene-α-L-lyxo-icosofuranoside 
• 33985-40-9 (3aR,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbaldehyde 
• 13298-99-2 D-O¹,O²,O³,O⁴-tetrabenzyl-galactitol 
• 105368-51-2 methyl 5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20-hexadecadeoxy-2,3-O-isopropylidene-α-L-lyxo-icosofuranoside 

Relevant academic research and scientific papers

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

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").