139563-66-9

Usage

Chemical class

Carbohydrates

Derivative of D-glucopyranose

Yes
It is a derivative of D-glucopyranose, a monosaccharide (simple sugar) that is the most common form of glucose.

Number of acetyl groups

Four
The compound has four acetyl groups attached to it, which are responsible for its reactivity and properties in organic synthesis.

Benzyl group attachment

3-O position
A benzyl group is attached to the 3-O position of the glucose molecule, which provides steric hindrance and influences the reactivity of the compound.

Building block in synthesis

Yes
It is commonly used as a building block in the synthesis of other complex organic molecules, particularly in the fields of medicinal chemistry and drug development.

Applications

Medicinal chemistry, drug development, and carbohydrate chemistry
Its unique structure and properties make it valuable for the creation of novel pharmaceutical compounds and as a tool for studying carbohydrate chemistry.

Use as a reagent

Organic synthesis and chemical research

Molecular weight

Approximately 520.55 g/mol
The molecular weight is an important property that can be used to determine the molar concentration of the compound in a solution.

Solubility

Soluble in organic solvents
The compound is soluble in organic solvents such as dichloromethane, acetone, and ethanol, which makes it suitable for use in various chemical reactions and purification techniques.

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 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 492-62-6 alpha-D-glucopyranose 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 100-44-7 benzyl chloride 
• 101475-83-6 3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 127-09-3 sodium acetate 

Downstream Products

• 124813-93-0 benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 87791-22-8 1-O-Acetyl-3-O-benzyl-2,4,6-tri-O-methyl-β-D-glucopyranose 
• 87791-21-7 1-O-Acetyl-3-O-benzyl-2,4,6-tri-O-methyl-α-D-glucopyranose 
• 80064-96-6 N⁴-acetyl-1-(2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl)cytosine 
• 124813-99-6 methyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl)-α-D-mannopyranoside 
• 124814-09-1 C₈₀H₈₆O₁₉ 
• 146530-62-3 ethyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside 
• 22331-16-4 phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside 
• 22331-15-3 phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranoside 
• 103082-79-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-α-D-glucopyranose 
• 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 
• 275817-29-3 (2R,4aR,6S,7R,8R,8aR)-8-Benzyloxy-6-dodecylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 275817-31-7 Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-dodecylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 

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

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.

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%.

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.

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.

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.

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.