544686-87-5

Upstream product

• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 106-95-6 allyl bromide 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 56083-15-9 (S)-4-((allyloxy)methyl)-2,2-dimethyl-1,3-dioxolane 
• 123-34-2 (R)-3-allyloxypropane-1,2-diol 

Downstream Products

• 544686-88-6 3-O-allyl-2-O-(2-azido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol 
• 1384160-46-6 2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-O-(tert-butyldiphenylsilyl)-sn-glycerol 
• 1384160-43-3 3-O-allyl-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-O-(tert-butyldiphenylsilyl)-sn-glycerol 
• 1384160-42-2 3-O-allyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-O-(tert-butyldiphenylsilyl)-sn-glycerol 
• 1384160-44-4 3-O-allyl-2-O-[2,3,4-tri-O-benzyl-6-O-(9H-fluoren-9-ylmethyloxycarbohyl)-α-D-glucopyranosyl]-1-O-(tert-butyldiphenylsilyl)-sn-glycerol 
• 1235579-96-0 1-O-(tert-butyldiphenylsilyl)-2-O-(2-O-(4-azidobenzyl)-3-O benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-3-O-allyl-sn-glycerol 
• 1235579-95-9 1-O-(tert-butyldiphenylsilyl)-2-O-(2-O-(4-methoxybenzyl)-3-O benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-3-O-allyl-sn-glycerol 
• 595605-55-3 (S)-(-)-3-tert-butyldiphenylsilyl-1-O-(1'-(Z)-hexadecenyl)-2-(2-trimethylsilanylethoxymethyl)glycerol 
• 849240-71-7 Phosphoric acid benzyl ester (S)-3-{benzyloxy-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propoxy]-phosphoryloxy}-2-(4-methoxy-benzyloxy)-propyl ester (S)-2,3-bis-benzyloxy-propyl ester 
• 544686-92-2 Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl ester 
• 544686-90-0 2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-allyl-1-O-tert-butyldiphenylsilyl-sn-glycerol 
• 849240-69-3 benzyl [(2S)-1,2-di-benzyloxy-propan-3-yl] [(2R)-1-tert-butyldiphenylsilyloxy-2-(4-methoxybenzyloxy)propan-3-yl] phosphate 

Relevant academic research and scientific papers

Regioselective phosphorylation of: Myo -inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol

A regioselective phosphorylation method for myo-inositol was developed by utilizing readily preparable BINOL-derived phosphoramidites. The method also facilitated the complete separation of the diastereomeric products by simple chromatography. Based on this phosphorylation and Ni-catalyzed alkyl-alkyl cross-coupling reaction for long fatty acids, we achieved the first synthesis of a lysophosphatidylinositol, EhPIa having long fatty acid C30:1, as a partial structure of glycosylphosphatidylinositol (GPI) anchor from the cell membrane of a protozoa, Entamoeba histolytica.

Synthesis of structural variants of Staphylococcus aureus lipoteichoic acid (LTA)

Based on 1,2-O-isopropylidene-sn-glycerol, which is readily available from d-mannitol, five chiral building blocks for the construction of structural variants of Staphylococcus aureus LTA designed and synthesized. Ligation of these building blocks led readily to the target molecules 1 and 2. They demonstrated that the d-alanine residues at the glycerophosphate backbone are decisive for the activation of the immune system.

Direct synthesis of plasmenylcholine from allyl-substituted glycerols

We report a new method for the facile preparation of plasmenylcholine via reaction of lithioalkoxy allyl intermediates with 1-iodoalkanes as the key step in the stereoselective formation of 1′-(Z)-alkenyl glyceryl ethers. The allyl anion intermediate is prepared by treating mono- or disiloxy-protected 1-allylglycerol precursors with s-BuLi at -65 to -80°C. Subsequent addition of 1-iodoalkane solutions at low temperature gives moderate yields of γ-coupled, Z-vinyl ethers as the major product and α-coupled product as the minor component. Several different preparative strategies for the total synthesis of plasmalogens are enabled by this simple transformation.