20770-84-7

Upstream product

• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 3458-28-4 D-Mannose 
• 159407-17-7 phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 119237-86-4 allyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 20746-71-8 Allyl 2,3-Bis-O-(phenylmethyl)-4,6-(phenylmethylene)-D-mannopyranoside 
• 48149-74-2 allyl D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 71925-96-7 allyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 145773-08-6 allyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 20746-64-9 allyl (R)-4,6-O-benzylidene-β-D-gluco-pyranoside 
• 2595-07-5 allyl β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 103833-57-4 allyl 4,6-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranoside 
• 93382-48-0 allyl 4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 1027636-76-5 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate 
• 556062-73-8 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl diethyl phosphite 
• 556062-75-0 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl N,N,N',N'-tetramethylphosphoroamidate 
• 1000813-74-0 4,6-O-benzylidene-2,3-di-O-benzyl-D-mannopyranosyl trichloroacetimidate 
• 1000813-71-7 2,4-dinitro-6-(methoxycarbonyl)phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-D-mannopyranoside 
• 6027-89-0 L-gulose 
• 159572-15-3 (2R,4S)-4-((1R,2R)-1,2-Bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-one 
• 1144104-32-4 (2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl) dibenzyl phosphate 
• 1144104-43-7 [2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl] dibenzyl phosphate 
• 1192219-57-0 p-methoxyphenyl (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside 
• 627509-50-6 allyl 2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranoside 

Relevant academic research and scientific papers

Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**

Despite many years of invention, the field of carbohydrate chemistry remains rather inaccessible to non-specialists, which limits the scientific impact and reach of the discoveries made in the field. Aiming to increase the availability of stereoselective

A Synthetic Carbohydrate-Protein Conjugate Vaccine Candidate against Klebsiella pneumoniae Serotype K2

Klebsiella pneumoniae causes pneumonia and liver abscesses in humans worldwide and contains virulence factor capsular polysaccharides and lipopolysaccharides linked to the cell wall. Although capsular polysaccharides are good antigens for vaccine producti

Synthetic heparin pentasaccharides

Preparation and use of synthetic monosaccharides, disaccharides, trisaccharides, tetrasaccharides and pentasaccharides useful for the preparation of synthetic heparinoids.

Highly stereoselective β-mannopyranosylation via the 1-α-glycosyloxy-isochromenylium-4-gold(I) intermediates

While the gold(I)-catalyzed glycosylation reaction with 4,6-O-benzylidene tethered mannosyl ortho-alkynylbenzoates as donors falls squarely into the category of the Crich-type β-selective mannosylation when Ph3PAuOTf is used as the catalyst, in that the mannosyl α-triflates are invoked, replacement of the -OTf in the gold(I) complex with less nucleophilic counter anions (i.e., -NTf2, -SbF6, -BF4, and -BAr4F) leads to complete loss of β-selectivity with the mannosyl ortho-alkynylbenzoate β-donors. Nevertheless, with the α-donors, the mannosylation reactions under the catalysis of Ph3PAuBAr4F (BAr4F=tetrakis[3,5-bis(trifluoromethyl)phenyl]borate) are especially highly β-selective and accommodate a broad scope of substrates; these include glycosylation with mannosyl donors installed with a bulky TBS group at O3, donors bearing 4,6-di-O-benzoyl groups, and acceptors known as sterically unmatched or hindered. For the ortho-alkynylbenzoate β-donors, an anomerization and glycosylation sequence can also ensure the highly β-selective mannosylation. The 1-α-mannosyloxy-isochromenylium-4-gold(I) complex (Cα), readily generated upon activation of the α-mannosyl ortho-alkynylbenzoate (1 α) with Ph3PAuBAr4F at -35 C, was well characterized by NMR spectroscopy; the occurrence of this species accounts for the high β-selectivity in the present mannosylation.

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.

A new method for selective deprotection of anomeric N,O -dimethylhydroxylamine promoted by TMSCl

TMSCl was shown to be an efficient reagent for selective deprotection of the anomeric position protected as N,O-dimethylhydroxylamine glycoside. This deprotection condition was proved to be compatible with a number of protecting groups, such as the TBDPS, acetyl, benzyl, benzylidene, and benzoyl groups.Copyright Taylor and Francis Group, LLC.

TANNIN INHIBITORS OF HIV

The invention provides a method to prevent or treat HIV-infection with synthetic tannins, and pharmaceutical compositions comprising synthetic tannins.

Trichloroisocyanuric acid (TCCA): An efficient green reagent for activation of thioglycosides toward hydrolysis

Trichloroisocyanuric acid (TCCA), an inexpensive, commercially available, and non-toxic reagent has been used for the activation of thioglycosides toward their hydrolysis to the corresponding hemiacetals in high to excellent yields. The methodology provides a mild reaction condition for dealing with compounds containing acid sensitive functional groups.

C-Glycosyl amino acids through hydroboration-cross-coupling of exo-glycals and their application in automated solid-phase synthesis

O-Glycosylation is one of the most important post-translational modifications of proteins. The attachment of carbohydrates to the peptide backbone influences the conformation as well as the solubility of the conjugates and can even be essential for binding to specific ligands in cell-cell interactions or for active transport over membranes. This makes glycopeptides an interesting class of compounds for medical applications. To enhance the long-term availability of these molecules in vivo, the stabilization of the glycosidic bond between the amino acid residue and the carbohydrate is of interest. The described modular approach affords β-linked C-glycosyl amino acids by a sequence of Petasis olefination of glyconolactones, stereoselective hydroboration and a mild B-alkyl-Suzuki coupling reaction. The coupling products were transformed to C-glycosyl amino acid building-blocks suitable for solid-phase synthesis and successfully incorporated into a partial sequence of the tumor-associated MUC1-glycopeptide. The resulting C-glycopeptides are candidates for the development of long-term stable mimics of O-glycopeptide vaccines. Copyright

A mild and general method for preparation of α-glycosyl chlorides

A mild and efficient chlorination method for production of glycosyl chlorides is first described which employs inexpensive trichlorotriazine (TCT) and DMF as a chlorination reagent and is compatible with typical acid-labile hydroxyl protecting functions. The scope and limitations, reaction mechanism and its application in the sequential glycosylations are discussed.