180403-91-2

Upstream product

• 545-06-2 trichloroacetonitrile 
• 155155-64-9 (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 187232-88-8 (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,4aR,6R,7R,8R,8aS)-7-hydroxy-2-phenyl-6-(2-trimethylsilanyl-ethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 187232-94-6 (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4S,5S,6R)-3-benzoyloxy-5-hydroxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 187232-91-3 (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,4aR,6R,7R,8S,8aS)-7-benzoyloxy-2-phenyl-6-(2-trimethylsilanyl-ethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 187233-03-0 (2S,4S,5R,6R)-4-Acetoxy-2-[(2R,3S,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzoyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and biological activities of three sulfated sialyl Le(x) ganglioside analogues for clarifying the real carbohydrate ligand structure of L-selectin

Sulfated sialyl Le(x) ganglioside analogues at C-6 of D-galactose, N-acetyl-D-glucosamine, and of both D-galactose and N-acetyl-D-glucosamine residues have been synthesized, in order to clarify the structure of the real carbohydrate ligand of L-selectin. Coupling of the suitably protected N-acetyl-D-glucosaminyl-β(1→3)-lactose derivatives 13 and 16 with the sialyl α(2→3)-D-galactopyranosyl trichloroacetimidates 10 and 12 (glycosyl donors), via glycosylation of 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-galactopyranoside (1) with the phenyl 2-thioglycoside derivative (2) of N-acetylneuraminic acid (Neu5Ac) using N-iodosuccinimide/TfOH, O-benzoylation, removal of the benzylidene group affording 5, selective 6-O-levulinoylation, O-benzoylation, removal of the 2-(trimethylsilyl)ethyl group, and imidate formation, or via O-acetylation of 5, removal of the 2-(trimethylsilyl)ethyl group, then imidate formation, gave the pentasaccharides 18-20. The glycosylation of the pentasaccharide accepters (21-23) derived from 18-20 by removal of the 4-methoxybenzyl group, with phenyl 1-thioglycoside derivative 27 of L-fucose using dimethyl(methylthio)sulfonium triflate (DMTST) afforded the corresponding hexasaccharides 28-30, which were transformed in good yields, via reductive removal of their benzyl groups, O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, imidate formation, coupling with (2S,3R,4E)-2-azido-O-benzoyl-4-octadecene-1,3-diol (35) in the presence of boron trifluoride etherate, selective reduction of the azido group, coupling with octadecanoic acid, selective removal of the levulinoyl groups, treatment with sulfur trioxide-pyridine complex, then removal of the protecting groups, into the desired sulfated sialyl Le(x) ganglioside analogues 50-52.