130325-14-3

Upstream product

• 20675-63-2 O⁶-Benzyl-α-D-galactopyranose 
• 108-24-7 acetic anhydride 
• 20675-63-2 6-O-benzyl-D-galactose 
• 100-39-0 benzyl bromide 
• 35526-05-7 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 52175-01-6 6-O-Benzyl-D-galactose 

Downstream Products

• 107855-14-1 ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside 
• 1403603-79-1 C₂₆H₃₄O₆S 
• 1403603-69-9 ethyl 6-O-benzyl-2-O-(4-methoxybenzyl)-thio-β-D-galactopyran-3,4-diol 
• 1403603-70-2 (R)-benzyl-2-((2R,3S,4S,5R,6S)-2-(benzyloxymethyl)-6-(ethylthio)-3-hydroxy-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoate 
• 1403603-80-4 (2R,3S,4S,5R,6S)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-2-(benzyloxymethyl)-6-(ethylthio)-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-yl benzoate 
• 1403603-81-5 (2R,3S,4R,5R,6S)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-2-(benzyloxymethyl)-6-(ethylthio)-5-hydroxytetrhydro-2H-pyran-3-yl benzoate 
• 1403603-71-3 (2R,3S,4S,5R,6S)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-5-(benzyloxycarbonyloxy)-2-(benzyloxymethyl)-6-(ethylthio)tetrahydro-2H-pyran-3-yl benzoate 
• 321540-98-1 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(4aR,6S,7R,8R,8aR)-7-acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 321540-86-7 methyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside 
• 290330-34-6 2,3,4-tri-O-acetyl-6-O-benzyl-α-D-galactopyranosyl bromide 

Relevant academic research and scientific papers

Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit

Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.

A practical approach to regioselective O-benzylation of primary positions of polyols

Exposure of saccharide polyols to a moderate excess of benzyl bromide and DIPEA at 90 °C results in the regioselective O-benzylation of primary positions in moderate to good yields. The reactions can be performed without inert atmosphere and provide synth

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.

Chemical synthesis of sulfated oligosaccharides with a β-D-Gal-(1→3)-[β-D-Gal-(1→4)-(α-L-Fuc-(1→3)-β-D-GlcNAc-(1→6)]-α-D -GalNAc sequence

The syntheses of two sulfated pentasaccharides: β-D-Gal6SO3Na-(1→3)-[β-D-Gal-(1→4)-α-L-Fuc-(1→3)-β-D-GlcNAc-(1→6) ]-α-D-GalNAc→OMe (1) and β-D-Gal6SO3Na-(1→3)-[β-D-Gal-(1→4)-α-L-Fuc-(1→3)-β-D-GlcNAc6SO3Na -(1→6)]-α-D-GalNA