79218-68-1

Upstream product

• 51532-75-3 3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 
• 100-44-7 benzyl chloride 
• 604-69-3 β-D-glucose pentaacetate 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 53270-12-5 1,2-O-(1-ethoxyethylene) 3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranose 
• 64-19-7 acetic acid 
• 32860-96-1 3,4,6-tri-O-benzyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside 
• 58341-67-6 methyl 2,4-di-O-benzyl-α-D-mannopyranoside 
• 65827-59-0 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride 
• 108869-64-3 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 
• 9005-25-8 starch 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranoside 
• 13242-53-0 acetobromomannose 
• 28140-37-6 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside 

Downstream Products

• 125085-08-7 methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 96323-28-3 methyl-2,3,4-tri-O-benzyl-6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 96323-23-8 benzyl 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 96323-23-8 benzyl 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 70255-93-5 Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 
• 96323-30-7 methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 89756-04-7 ((2S,3S,4S,5R,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester 
• 89756-03-6 ((2R,3S,4S,5R,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester 
• 108869-64-3 3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate 
• 180714-32-3 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 152871-96-0 phenyl 1-deoxy-2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 343565-50-4 2-acetyl-3,4,6-tri-O-benzylglucopyranose-N-tosylcarbamate 
• 612499-94-2 allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 851366-19-3 Acetic acid (3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trifluoro-N-phenyl-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2-Aryl-1,3-dithiane 1-Oxide?

A new dehydrative glycosylation reaction has been established by capitalizing on the comproportionation reaction of 2-aryl-1,3-dithiane 1-oxides promoted by triflic anhydride (Tf2O). By wedding the high potency of thiophilic promoter system with the step efficiency of dehydrative glycosylation, this reagent underwent facile intermolecular oxothio acetalization with C1-hemiacetal donor to install a temporary leaving group, rendering a transient electrophilic center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3-diol protection. Most importantly, this method further provided a fresh perspective for the application of sulfur chemistry to carbohydrate chemistry.

Synthesis of Azido-Glycans for Chemical Glycomodification of Proteins

Chemically produced, accurately linkable oligosaccharides are of importance for the synthesis of neo-glycoproteins. On the route to high-mannose type N-glycans, we present a convenient synthesis of several glycans bearing an azide moiety at the reducing end. An azido-glycan core structure as valuable precursor was modified into the protected N-glycan pentasaccharide core structure and the possibility of modular attachment of different antenna was demonstrated through synthesis of a pentamannose donor and glycosylation with the core structure. The azido function allows for chemical ligation with recombinantly modified proteins featuring noncanonical cyclooctyne amino acids, providing access to customized glycopatterns of glycoproteins, e.g., of antibodies that are of high interest for biopharmaceutical applications.

Targeted delivery of fluorescent high-mannose-type oligosaccharide cathepsin inhibitor conjugates

Abstract Three fluorescent cathepsin inhibitor glycoconjugates have been designed, synthesized, and evaluated in terms of their cell internalization and cathepsin inhibitory properties. The conjugates are composed of a peptide epoxysuccinate, capable of c

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.

Intramolecular aglycon delivery for (1 → 2)-β-mannosylation: Towards the synthesis of phospholipomannan of Candida albicans

A high yielding method for 1,2-cis-β-D-mannosylation by intra-molecular aglycon delivery (IAD) through p-methoxy benzyl ether/acetal exchange and phenylsulfoxide donor is reported, along with its application in iterative assembly of antigenic (1 → 2)-β-pe

Expedient and versatile formation of novel amino-deoxy-ketoheptuloses

Novel monoketoheptuloses have been synthesized employing an amination step in a pre- and/or post-C1 chain elongation using a Petasis reagent by starting from aldohexoses or aldohexosamines. A series of gluco and manno configured 1-/3-deoxy-1-/3-amino-keto

'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

Synthesis of truncated analogues for studying the process of glycosyl phosphatidylinositol modification

Figure presented Many eukaryotic proteins are modified with a glycosylphosphatidylinositol (GPI) anchor at their C-termini. This post-translational modification causes these proteins to be noncovalently tethered to the plasma membrane. The synthesis of tr

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.