178454-13-2

Upstream product

• 608-68-4 dimethyl L-tartrate 
• 169532-17-6 ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside 
• 116514-50-2 ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 
• 100-39-0 benzyl bromide 
• 132799-10-1 ethyl 1-thio-α-L-fucopyranoside 

Downstream Products

• 1403603-68-8 (2R)-2-{(2S,3R,4S,5S,6R)-2-[(2R,3R)-1,4-dimethoxy-1,4-dioxo-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)butan-2-yloxy]-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy}-3-phenylpropanoic acid 
• 1403603-65-5 (2R,3R)-dimethyl-2-(3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate 
• 1403603-73-5 (2R,3R)-dimethyl 2-((2S,3R,4S,5S,6R)-5-(benzoyloxy)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-3-(benzyloxycarbonyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-((2S,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate 

Relevant academic research and scientific papers

Acyclic tethers mimicking subunits of polysaccharide ligands: Selectin antagonists

We report on the design and synthesis of molecules having E- and P-selectins blocking activity both in vitro and in vivo. The GlcNAc component of the selectin ligand sialyl LewisX was replaced by an acyclic tether that links two saccharide units. The minimization of intramolecular dipole-dipole interactions and the gauche effect would be at the origin of the conformational bias imposed by this acyclic tether. The stereoselective synthesis of these molecules, their biochemical and biological evaluations using surface plasmon resonance spectroscopy (SPR), and in vivo assays are described. Because the structure of our analogues differs from the most potent E-selectin antagonists reported, our acyclic analogues offer new opportunities for chemical diversity.

A new approach to explore the binding space of polysaccharide-based ligands: Selectin antagonists

The discovery of molecules that interfere with the binding of a ligand to a receptor remains a topic of great interest in medicinal chemistry. Herein, we report that a monosaccharide unit of a polysaccharide ligand can be replaced advantageously by a conformationally locked acyclic molecular entity. A cyclic component of the selectin ligand Sialyl Lewisx, GlcNAc, is replaced by an acyclic tether, tartaric esters, which link two saccharide units. The conformational bias of this acyclic tether originates from the minimization of intramolecular dipole-dipole interaction and the gauche effect. The evaluation of the binding of these derivatives to P-selectin was measured by surface plasmon resonance spectroscopy. The results obtained in our pilot study suggest that the discovery of tunable tethers could facilitate the exploration of the carbohydrate recognition domain of various receptors.