39686-94-7

Usage

Uses

Used in Organic Synthesis:
1,2,4,6-TETRA-O-ACETYL-3-O-BENZYL-BETA-D-GLUCOPYRANOSE is used as a building block for the preparation of various carbohydrate-based molecules. Its unique structure allows for the synthesis of complex carbohydrates and glycoconjugates, which are essential in many biological processes and have potential applications in pharmaceuticals and materials science.
Used in Chemical Research:
In the field of chemical research, 1,2,4,6-TETRA-O-ACETYL-3-O-BENZYL-BETA-D-GLUCOPYRANOSE serves as a valuable intermediate for the development of new synthetic methods and strategies. Its functional groups can be selectively modified, enabling the exploration of novel reactions and the synthesis of diverse carbohydrate derivatives.
Used in Biological Studies:
1,2,4,6-TETRA-O-ACETYL-3-O-BENZYL-BETA-D-GLUCOPYRANOSE is also utilized in biological studies to investigate the role of carbohydrates in various biological systems. Its ability to be modified allows researchers to create analogs of natural sugars, which can be used to study carbohydrate recognition, binding, and signaling processes.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 1,2,4,6-TETRA-O-ACETYL-3-O-BENZYL-BETA-D-GLUCOPYRANOSE is employed as a starting material for the synthesis of glycoconjugate drugs. These drugs have the potential to target specific biological receptors and exhibit improved pharmacokinetic properties, making them valuable candidates for the treatment of various diseases.
Used in Materials Science:
1,2,4,6-TETRA-O-ACETYL-3-O-BENZYL-BETA-D-GLUCOPYRANOSE also finds applications in materials science, where it can be used to develop carbohydrate-based materials with unique properties. These materials may have potential uses in areas such as sensors, coatings, and biocompatible materials for medical applications.

Upstream product

• 10230-17-8 O³-benzyl-D-glucose 
• 108-24-7 acetic anhydride 
• 65877-63-6 3-O-benzyl-D-glucopyranose 
• 97590-76-6 benzyl-O-β-D-glucopyranoside 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 101475-83-6 3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 127-09-3 sodium acetate 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 492-62-6 alpha-D-glucopyranose 

Downstream Products

• 39708-09-3 methyl-(O³-benzyl-O²,O⁴,O⁶-trimethyl-ξ-D-glucopyranoside) 
• 34339-69-0 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide 
• 180072-37-1 2,3,4-tri-O-acetyl-6-O-benzylglucosyl bromide 
• 275817-27-1 Acetic acid (2R,3R,4S,5R,6S)-5-acetoxy-2-acetoxymethyl-4-benzyloxy-6-dodecylsulfanyl-tetrahydro-pyran-3-yl ester 
• 128848-51-1 phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside 
• 679800-18-1 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-3-O-benzyl-1-thio-β-D-glucopyranoside 
• 679800-20-5 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-[2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->6)]-3-O-benzyl-1-thio-β-D-glucopyranoside 
• 182423-85-4 C₅₀H₇₀O₁₂ 
• 182423-83-2 C₅₀H₇₀O₁₂ 
• 40010-11-5 methyl β-D-glucopyranoside 3-benzyl ether 
• 81348-19-8 methyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside 
• 1372631-51-0 methyl 3-O-benzyl-6-O-trityl-β-D-glucopyranoside 
• 1372631-55-4 methyl 3-O-benzyl-2,4-di-O-(trifluoromethanesulfonyl)-6-O-trityl-β-D-glucopyranoside 
• 1372631-67-8 N-benzyl-3-O-benzyl-2,4-dideoxy-2,4-imino-D-talitol 

Relevant academic research and scientific papers

Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups

The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction suffers from poor functional group compatibility and limits their use as a protecting group. The visible-light-mediated debenzylation disclosed here renders benzyl ethers temporary protective groups, enabling new orthogonal protection strategies. Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time can be reduced from hours to minutes in continuous flow.

Synthesis of helicobacter-pylorus O2 serotype O antigen oligosaccharide compound

The invention discloses discloses synthesis of a helicobacter-pylorus O2 serotype O antigen oligosaccharide compound, and belongs to the field of organic synthesis. According to the synthesis, helicobacter-pylorus O2 serotype O-antigen disaccharide to tet

Total synthesis of viscumneoside III of Viscum coloratum

The first total synthesis of viscumneoside III, a promising anti-angina pectoris dihydroflavone O-glycoside isolated from Viscum coloratum was described here. Trichloroaceti-midate was employed as the apiofuranosyl donor to construct the key building block of homoeriodictyol-7-O-β-D-apiosyl-(1 → 2)-β-D-glycoside (1). The longest linear sequence (from 2 to 1) in the synthetic route required thirteen steps and afforded the final product 1 with an overall yield of 6.3%.

Preparation method of clostridium bolteae surface capsular polysaccharide structure derivative

The invention discloses a preparation method of a clostridium bolteae surface capsular polysaccharide structure derivative and belongs to the field of sugar chemistry. The preparation method comprisesthe following steps: taking glucose as a glycosyl donor to obtain a target beta-glycosidic bond; then successfully synthesizing a disaccharide building block through an oxidization-reduction glucoseC-2 site method; then synthesizing a target oligosaccharide structure which takes the disaccharide building block as a repeating unit, such as the gram-positive bacterium surface capsular polysaccharide structure derivative [arrow3]-alpha-D-Manp-(1arrow4)-beta-D-Rhap-(1arrow]5-Linker. A reducing end of decaose is connected with a connecting arm and is used for connecting protein to form a glycoconjugate for carrying out immunology researches. The method provided by the invention has the advantages of simplicity, time saving, labor saving and low cost; the obtained clostridium bolteae surface capsular polysaccharide structure derivative is possibly used for developing and preparing medicine related to autism.

Automated glycan assembly of a s. pneumoniae serotype 3 cps antigen

Vaccines against S. pneumoniae, one of the most prevalent bacterial infections causing severe disease, rely on isolated capsular polysaccharide (CPS) that are conjugated to proteins. Such isolates contain a heterogeneous oligosaccharide mixture of differe

Azetidine iminosugars from the cyclization of 3,5-Di- O -triflates of α-furanosides and of 2,4-Di- O -triflates of β-pyranosides derived from glucose

Primary amines with either 3,5-di-O-ditriflates of α-furanosides or 2,4-di-O-triflates of β-pyranosides form bicyclic azetidines in high yield.

The Glc2Man2-fragment of the N-glycan precursor - A novel ligand for the glycan-binding protein malectin?

The Glcα(1→3)Glcα(1→3)Manα(1→2)Man tetrasaccharide (Glc2Man2-fragment), a substructure of the natural N-glycan precursor, was synthesized. The interaction of this fragment with the protein malectin, a carbohydrate binding protein localized in the endoplasmatic reticulum, was investigated by 1H15N HSQC experiments and isothermal calorimetry. The chemical shift perturbations of nuclei in the protein's backbone caused by the binding of the Glc 2Man2-fragment to malectin suggest a binding mode like the known ligand nigerose. The Royal Society of Chemistry 2010.

Multi-gram synthesis of a hyaluronic acid subunit and synthesis of fully protected oligomers

Fully protected tetra-, hexa- and octasaccharides of hyaluronic acid were synthesized on a scale of several 100 mg up to gram quantities using allyl (methyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)- (1→3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D- glucopyranoside as a key building block. This disaccharide was subjected to deprotection, then glycosylation via the trichloroacetimidate method was employed to achieve the formation of the oligosaccharides.

First Synthesis of a Trisaccharide of Glycosylkaemferide: A Resistance Factor in Carnations

A trisaccharide, phenyl β-D-glucopyranosyl-(1→2)-[α -L-rhamnopyranosyl-(1→6)]-1-thio-β-D-glucopyranoside, of glycosylkaemferide, a resistance factor in carnations, was synthesized in a practical way.

Synthesis of glycyrrhetic acid diglycosides and their cytoprotective activities against CCl4-induced hepatic injury in vitro

Glycyrrhetic acid diglycosides 16, 24, 25, 42 and 46, with respectively β-D-glucuronopyranosyl-(1→3)-β-D-glucopyranose, -(1→6)-α-D-glucopyranose, -(1→6)-β-D-glucopyranose, -(1→6)-β-D-galactopyranose, and β-D-galacturonopyranosyl-(→2)-β-D-glucopyranose as sugar components at the O-3 positions on the aglycons, were synthesized. In vitro cytoprotective activities, against CCl4-induced hepatic injury, of the synthetic diglycosides, methyl β-D-glucuronopyranosyl-(1→4)-α-D-glucopyranosyl-D-glycyrrhe tinate 33 and methyl esters 15 and 23 (the precursors of 16 and 24 respectively) were compared with those of glycyrrhizin 1 and β-D-glucuronopyranosyl-(1→2)-β-D-glucopyranosyl-glycyrrhetic acid 2. Of the glycosides 16, 24, and 25, with β-D-glucuronopyranosylglucopyranose as the sugar component, 16 and 24 were as cytoprotective as 1 and 2, whereas 25 showed no remarkable activity. From stereomodels of the glycosides these differences in activity were inferred to be due to the stereochemistries of the terminal β-D-glucuronopyranoses in the molecules. Glycoside 46, in which the terminal β-D-glucuronopyranose of 2 was replaced by β-D-galacturonopyranose, was as potent as 2. Further, it was confirmed that a free COOH group on the E ring of aglycon was essential for the activity.