20675-63-2

Upstream product

• 35526-05-7 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 100-39-0 benzyl bromide 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 70932-43-3 (3aS,5S,5aR,8aR,8bS)-5-(benzyloxymethyl)-2,2,7,7-tetramethyltetrahydro-3aH-bis-[1,3]-dioxolo-[4,5-b:4',5'-d]-pyran 
• 110319-61-4 1,2:3,4-di-O-isopropylidene-β-D-galactopyranose 
• 59-23-4 D-Galactose 
• 10257-28-0 D-Galactose 
• 35526-05-7 6-O-benzyl-1,2-3,4-di-O-isopropylidene-D-galactopyranoside 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 23397-86-6 6-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 20675-64-3 O⁶-Benzyl-D-galactose-diethyldithioacetal 
• 130325-14-3 1,2,3,4-tetra-O-acetyl- 6-O-benzyl-α-D-galactopyranoside 
• 290330-34-6 2,3,4-tri-O-acetyl-6-O-benzyl-α-D-galactopyranosyl bromide 
• 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 
• 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 
• 116167-60-3 S-ethyl-6-O-(phenylmethyl)-1-thio-β-D-galactopyranoside 
• 130034-84-3 6-O-Benzyl-2,3,4-tri-O-acetyl-α-D-glucopyranosyl chloride 
• 104629-47-2 (1R,2R,3S)-5-oxo-3-<(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy>cyclohex-4-ene-1,2-N-phenyldicarboximide 
• 104629-47-2 (1S,2S,3R)-5-Oxo-N-phenyl-3-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyloxy)cyclohexane-1,2-dicarboximide 
• 130034-75-2 (1S,2S,3R)-3-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-5-oxo-N-phenylcyclohexane-1,2-dicarboximide 
• 130034-75-2 (1R,2R,3S)-3-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-β-D-glucopyranosyloxy)-5-oxo-N-phenylcyclohexane-1,2-dicarboximide 
• 130034-78-5 (3S)-3-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-β-D-glucopyranosyloxy)-5-(t-butyldimethylsiloxy)cyclohex-4-ene-1,1,2,2-tetracarbonitrile 
• 130034-77-4 (3S)-3-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-5-(t-butyldimethylsiloxy)cyclohex-4-ene-1,1,2,2-tetracarbonitrile 
• 130034-79-6 (3R)-3-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-β-D-glucopyranosyloxy)-5-(t-butyldimethylsiloxy)cyclohex-4-ene-1,1,2,2-tetracarbonitrile 

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.

Synthetic MUC1 antitumor vaccine with incorporated 2,3-sialyl-T carbohydrate antigen inducing strong immune responses with isotype specificity

The endothelial glycoprotein MUC1 is known to underlie alterations in cancer by means of aberrant glycosylation accompanied by changes in morphology. The heavily shortened glycans induce a collapse of the peptide backbone and enable accessibility of the latter to immune cells, rendering it a tumor-associated antigen. Synthetic vaccines based on MUC1 tandem repeat motifs, comprising tumor-associated 2,3-sialyl-T antigen, conjugated to the immunostimulating tetanus toxoid, are reported herein. Immunization with these vaccines in a simple water/oil emulsion produced a strong immune response in mice to which stimulation with complete Freund’s adjuvant (CFA) was not superior. In both cases, high levels of IgG1 and IgG2a/b were induced in C57BL/6 mice. Additional glycosylation in the immunodominant PDTRP domain led to improved binding of the induced antisera to MCF-7 breast tumor cells, compared with that of the monoglycosylated peptide vaccine.

1,2;3,4-Di-O-isopropylidene-l-galactose synthesis from its d-enantiomer

Easy procedure was devised to obtain di-O-isopropylidene-l-galactose from di-O-isopropylidene-d-galactose.

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.

Modifying the regioselectivity of glycosynthase reactions through changes in the acceptor

Successful glycosynthase-mediated reactions have been performed on 6-O-benzyl-, 6-O-(4-nitrobenzyl)-, and 6-O-benzoyl-D-glucopyranose to give 1,2-β- and 1,3-β-D-glycosylated products; 4-O-benzyl-D-xylopyranose gave only a 1,2-β-glycosylated product. A rat

Synthesis of a tumor-associated 2,3-sialyl-T glycododecapeptide antigen from the tandem repeat region of the mucin MUC1

As a cell surface antigen for the development of selective antitumor vaccines, a tumor-associated glycododecapeptide from epithelial MUC1 carrying the 2,3-sialyl-T antigen was synthesized. The 2,3-ST building block was assembled from a TN-threo

Syntheses of novel photoaffinity probes for bioorganic studies on nyctinasty of leguminous plants

Novel and non-radioactive photoaffinity probes (1 and 2) for the bioorganic study of nyctinasty are designed and synthesized based on potassium isolespedezate (3), which induce leaf-opening against the leaf of Cassia mimosoides L. These probes bear a trifluoromethyldiazirine or diazophenyl group for photoaffinity and a biotin subunit for affinity chromatography and chemiluminescent detection. Probes (1 and 2) showed leaf-opening activity at 5×10-5 mol/L with leaves of C. mimosoides; thus, they would be an important tool for the identification of a receptor protein for 3.

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

An economical synthesis of Lewis X, sialyl lewis X and their α-galactosyl analogues

Economical syntheses of the Lewis X trisaccharide 8 and sialyl Lewis X tetrasaccharide 18 epitopes and the syntheses of the α-galactosyl epimers 9 and 20 of these structures are described. Thioglycosides 2, 5, 11 and 15 were used as glycosyl donors to con

Application of glycals to the synthesis of oligosaccharides: Convergent total syntheses of the Lewis X trisaccharide sialyl Lewis X antigenic determinant and higher congeners

Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLex tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The us