68681-00-5

Upstream product

• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl 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 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 225924-46-9 1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide 
• 80877-03-8 3,4,6-tri-O-acetyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose 
• 83-87-4 D-Mannose pentaacetate 
• 13242-53-0 acetobromomannose 
• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 29073-91-4 1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 67-56-1 methanol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 69435-20-7 C₅₀H₆₂O₉ 
• 79218-68-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 135583-76-5 phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 
• 213028-88-7 1-O-acetyl-3,4,6-tri-O-benzyl-α,β-D-glucopyranose 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 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 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 

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.

Mannosylated compounds useful for the prevention and the treatment of infectious diseases

The present invention relates to new anti-infectious compounds consisting of (i) a polar head having from one to three mannose, dimannose or trimannose moieties, which is coupled through an appropriate linker to (ii) a single lipid chain of at least 17 carbon atoms of length. Pharmaceutical compositions and therapeutic uses thereof are also provided.

'Naked' and hydrated conformers of the conserved core pentasaccharide of N-linked glycoproteins and its building blocks

N-glycosylation of eukaryotic proteins is widespread and vital to survival. The pentasaccharide unit -Man3GlcNAc2- lies at the protein-junction core of all oligosaccharides attached to asparagine side chains during this process. Although its absolute conservation implies an indispensable role, associated perhaps with its structure, its unbiased conformation and the potential modulating role of solvation are unknown; both have now been explored through a combination of synthesis, laser spectroscopy, and computation. The proximal -GlcNAc-GlcNAc- unit acts as a rigid rod, while the central, and unusual, -Man-β-1,4-GlcNAc- linkage is more flexible and is modulated by the distal Man-α-1,3- and Man-α-1,6- branching units. Solvation stiffens the 'rod' but leaves the distal residues flexible, through a β-Man pivot, ensuring anchored projection from the protein shell while allowing flexible interaction of the distal portion of N-glycosylation with bulk water and biomolecular assemblies.

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.

Preparation of Thiosugars and Their Use

A process for the preparation of a thiosaccharide represented by Saccharide-S-H wherein Saccharide comprises at least 4 sugar units, comprises subjecting a corresponding compound of the formula (P)Saccharide-S-(P) wherein (P) represents an O- or S-protecting group(s), to Birch reduction.

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.