130694-47-2

Upstream product

• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 103002-29-5 3,4,6-Tri-O-acetyl-α-D-galactopyranose 1,2-(exo-methyl orthoacetate) 
• 4163-60-4 β-D-galactose peracetate 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 67-56-1 methanol 
• 100-44-7 benzyl chloride 
• 13242-53-0 acetobromomannose 
• 83-87-4 D-Mannose pentaacetate 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 29073-91-4 (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 

Downstream Products

• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 138925-14-1 phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 135583-76-5 phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 
• 384819-72-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 
• 148968-89-2 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-mannopyranose 
• 405219-53-6 allyl (2-azido-3,4,6-tri-O-benzyl-2-deoxy)-β-D-mannopyranoside 
• 90302-53-7 Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 1360560-48-0 (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-ethyl-3aH,5H,6H,7H,7aH-pyrano[2,3-d][1,3]oxazole 
• 634197-71-0 p-methylphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranose 
• 793672-55-6 p-methylphenyl 3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside 
• 108869-64-3 3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate 
• 125209-24-7 phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(3,4,6-tri-O-benzyl-2-O-(methylthio)thiocarbonyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 125209-22-5 methyl 2-O-benzyl-6-deoxy-4-O-methyl-3-O-(3,4,6-tri-O-benzyl-2-O-(methylthio)thiocarbonyl-β-D-glucopyranosyl)-β-D-galactopyranoside 
• 125085-04-3 methyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-O-benzyl-6-deoxy-4-O-methyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates

Boron neutron capture therapy (BNCT) is a noninvasive binary therapeutic modality applicable to the treatment of cancers. While BNCT offers a tumor-targeting selectivity that is difficult to match by other means, the last obstacles preventing the full har

ANTIBODY CONJUGATES AND METHODS OF MAKING THE ANTIBODY CONJUGATES

Described herein are antibody conjugates and methods of making antibody conjugates.

Exploring glycosylation reactions under continuous-flow conditions

The industrial development of carbohydrate-based drugs is greatly thwarted by the typical challenges inherent in oligosaccharide synthesis. The practical advantages of continuous-flow synthesis in microreactors (high reproducibility, easy scalability, and fast reaction optimization) may offer an effective support to make carbohydrates more attractive targets for drug-discovery processes. Here we report a systematic exploration of the glycosylation reaction carried out under microfluidic conditions. Trichloroacetimidates and thioglycosides have been investigated as glycosyl donors, using both primary and secondary acceptors. Each microfluidic glycosylation has been compared with the corresponding batch reaction, in order to highlight advantages and drawbacks of microreactors technology. As a significant example of multistep continuous-flow synthesis, we also describe the preparation of a trisaccharide by means of two consecutive glycosylations performed in interconnected microreactors.

Disaccharide-containing macrocycles by click chemistry and intramolecular glycosylation

In this study o- and m-xylylene moieties in combination with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyra

Synthetic oligosaccharides as tools to demonstrate cross-reactivity between polysaccharide antigens

Escherichia coli O148 is a nonencapsulated enterotoxigenic (ETEC) Gram negative bacterium that can cause diarrhea, hemorrhagic colitis, and hemolytic uremic syndrome in humans. The surface-exposed O-specific polysaccharide (O-SP) of the lipopolysaccharide

Neighboring-group participation by C-2 ether functions in glycosylations directed by nitrile solvents

Ether-protecting functions at C-2 hydroxy groups have been found to play participating roles in glycosylations when the reactions are conducted in nitrile solvent mixtures. The participation mechanism is based on intramolecular interaction between the lone electron pair of the oxygen atom of the C-2 ether function and the nitrile molecule when they are positioned in a cis configuration. A 1,2-cis glycosyl oxazolinium intermediate is formed. This participation, in conjunction with the anomeric effect of the glycosyl donor, confers high 1,2-trans selectivities on glycosylations. Further application of this concept has led to efficient preparations of α-(1→5)-arabinan oligomers.

Isolation, structure elucidation, total synthesis, and evaluation of new natural and synthetic ceramides on human SK-MEL-1 melanoma cells

Two new long-chain ceramides, trametenamides A (1) and B (2), were isolated from the methanolic extract of the fruiting body of the fungus Trametes menziesii. The structures were elucidated by spectroscopic analyses and chemical transformations, and the absolute stereochemistry of trametenamide B (2) was determined by stereoselective total synthesis of four possible diastereomers. The acetyl derivative of the natural ceramide (1a) and synthetic ceramides (24-27) showed cytotoxicity on the human melanoma cell line SK-MEL-1, which was caused by induction of apoptosis as determined by DNA fragmentation, poly-(ADP-ribose) polymerase cleavage, and procaspase-9 and -8 processing.

1,2-Anhydrosaccharides and 1,2-cyclic sulfites as saccharide donors in convergent synthesis of glucopyranosyl-, mannopyranosyl- and ribofuranosylbenzocamalexin

A convergent synthesis of 1-(β-o-glucopyranosyl)-, 1-(α-D-mannopyranosyl)- and 1-(β-D-ribofuranosyl) benzocamalexin was elaborated as an alternative route to the linear approach based on the indoline-indole method. 1,2-Anhydrosaccharides and 1,2-cyclic sulfites as saccharide donors were used in the key glycosylation step. Coupling with benzocamalexin resulted in moderate to excellent yields of nucleoside analogs, depending on the saccharide donor, catalyst and solvent used.

A convenient multigram preparation of functionalized 2-azido-2-deoxy-D-mannose as a useful orthogonally protected building block for oligosaccharide synthesis

Multigram preparation of strategically protected 2-azido-2-deoxy mannose 5 from pentaacetyl glucose 1 is described. This manno-derivative was obtained in a straightforward manner and in high overall yield and represents a flexible building-block for complex oligosaccharide synthesis.

Synthesis of the C-glycosidic analogue of adenophostin A and its uracil congener as potential IP3 receptor ligands. Stereoselective construction of the C-glycosidic structure by a temporary silicon-tethered radical coupling reaction

Synthesis of the C-glycosidic analogue 9 of adenophostin A, a very potent IP3 receptor agonist, and its uracil congener 10 was achieved via a temporary silicon-tethered radical coupling reaction as the key step. Phenyl 3,4,6-tri-O-(p-methoxyben