54325-28-9

Usage

Uses

Used in Organic Synthesis:
6-O-TRIPHENYLMETHYL-ALPHA-D-GLUCOPYRANOSE is used as a protective group for hydroxyl groups in organic synthesis, allowing for selective chemical reactions to take place. The triphenylmethyl group attached to the glucose molecule masks the reactivity of hydroxyl groups, enabling chemists to perform specific reactions without affecting other parts of the molecule.
Used in Biochemistry:
In biochemistry, 6-O-TRIPHENYLMETHYL-ALPHA-D-GLUCOPYRANOSE is used to protect the glucose molecule from enzymatic degradation. The steric hindrance provided by the triphenylmethyl group prevents enzymes from accessing and breaking down the glucose molecule, making it a valuable tool in studying the interactions between sugars and enzymes.
Used in Pharmaceutical Industry:
6-O-TRIPHENYLMETHYL-ALPHA-D-GLUCOPYRANOSE is used as a building block in the synthesis of complex carbohydrates and glycoconjugates, which are important components of many biologically active molecules. Its protective group properties allow for the controlled assembly of these complex structures, facilitating the development of new drugs and therapeutic agents.
Used in Materials Science:
In materials science, 6-O-TRIPHENYLMETHYL-ALPHA-D-GLUCOPYRANOSE can be used to create self-assembling structures and supramolecular systems. The triphenylmethyl group provides a hydrophobic moiety, while the glucose molecule offers hydrophilic interactions, enabling the formation of organized structures with potential applications in drug delivery, sensors, and other areas.
Used in Analytical Chemistry:
6-O-TRIPHENYLMETHYL-ALPHA-D-GLUCOPYRANOSE can be employed as a derivatizing agent in analytical chemistry, enhancing the detection and analysis of carbohydrates and related compounds. Its unique structure allows for selective derivatization, improving the sensitivity and selectivity of analytical methods.

Upstream product

• 50-99-7 D-glucose 
• 76-83-5 trityl chloride 
• 2280-44-6 D-Glucose 
• 492-62-6 alpha-D-glucopyranose 
• 3458-28-4 D-Mannose 
• 59-23-4 D-Galactose 
• 7322-31-8 β-D-mannose 
• 15572-79-9 aldehydo-L-Galactose 
• 10257-28-0 D-Galactose 

Downstream Products

• 22331-13-1 1,2,3,6-tetra-O-acetyl-4-O-benzyl-β-D-glucopyranose 
• 99337-73-2 1,2,3,6-tetra-O-acetyl-4-O-trityl-β-D-glucopyranose 
• 79414-65-6 1,2,3,6-tetra-O-acetyl-4-O-benzyl-α-D-glucopyranose 
• 108257-55-2 1,2,3,4-tetra-O-acetyl-6-O-benzyl-β-D-glucopyranose 
• 108257-52-9 1,2,3,4-tetra-O-acetyl-6-O-benzyl-α-D-glucopyranose 
• 108257-54-1 1,2,3,6-tetra-O-acetyl-4-O-trityl-α-D-glucopyranose 
• 13100-46-4 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose 
• 13100-46-4 1,2,3,4-tetra-O-acetyl-α-D-glucopyranoside 
• 92621-31-3 1,2,3,4-tetra-O-acetyl-6-O-triphenylmethyl-β-D-mannopyranose 
• 247017-29-4 1,2,3,4-tetra-O-benzoyl-6-O-trityl-α,β-D-glucopyranoside 
• 39687-22-4 benzyl 6-O-trityl-2,3,4-tri-O-benzyl-D-glucopyranoside 
• 27851-28-1 (2R,3R,4S,5R,6R)-2,3,4,5-tetrakis(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran 

Relevant academic research and scientific papers

Effect of branching density on avidity of hyperbranched glycomimetics for mannose binding lectin

Hyperbranched glycopolymers containing mannose units in the branch point were synthesized through the copolymerization of a mannose inimer and mannose acrylate via atom transfer radical polymerization (ATRP). Incorporating a saccharide residue at the branch point results in a closer analogue to natural branched polysaccharides. Gel permeation chromatography characterization of the polymers qualitatively indicates branching in samples from polymerizations utilizing the mannose inimer. Deprotection of the acetate protecting groups from the hyperbranched mannose polymers yields water-soluble polymers that interact with mannose binding lectin (MBL), a key protein of the innate immunity complement system. MBL interaction increases with increasing polymer molecular weight and increasing branching density. Notably, incorporating mannose into the branching repeat unit also increases the interaction of the glycopolymers with MBL compared with glycopolymers with the same branching density but with no mannose at the branch point.

Guanidine-containing molecular transporters: Sorbitol-based transporters show high intracellular selectivity toward mitochondria

(Figure Presented) Special delivery: Transporters constructed on a sorbitol scaffold with eight guanidine residues show significant translocation across the cell membrane and the blood-brain barrier and high affinities toward mitochondria in HeLa and KG1a

INHIBITORS OF MALARIAL AND PLASMODIUM FALCIPARUM HEXOSE TRANSPORTER AND USES THEREOF

Provided are molecules capable of binding to binding pockets of Plasmodium falciparum hexose transporter (PfHT) or analogs thereof and complexes comprising the same. Also provided herein are inhibitors of PfHT, pharmaceutical compositions comprising the i

MONOMETHYL FUMARATE-CARRIER CONJUGATES AND METHODS OF THEIR USE

Disclosed are conjugates of monomethyl fumarate and a carrier group or aminocarrier group, or a pharmaceutically acceptable salt thereof. In the conjugates, monomethyl fumarate acyl is covalently bonded to the carrier group or aminocarrier group through a

Total synthesis of agalloside, isolated from: Aquilaria agallocha, by the 5-O-glycosylation of flavan

Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic strategy holds promise for use in the synthesis of 5-O-glycosylated flavonoids. The synthesized agalloside (1) accelerated neural stem cell differentiation, which is a result comparable to that for the naturally occurring compound 1.

Synthetic method of gentiobiose

The invention provides a synthetic method of gentiobiose. The synthetic method of the gentiobiose comprises the following steps: taking D-glucose as a starting material; respectively synthesizing into beta-1,2,3,4-tetra-acetylated glucose and glucose-B-glucosinolate; and carrying out coupled reaction and then carrying out deprotection to generate the gentiobiose. The controllability of the technological process is high, isomerization of the product is avoided, the yield of single-step reaction is high, and the gentiobiose is suitable for being produced on a large scale. The separating efficiency of a final product is improved. By the chemical method, large-scale production of the gentiobiose is implemented, a biological-method complicated purification process is overcome, the production period is shortened, the cost is reduced, and the purity of the product is improved.

pyrimidine, pyrazole and pyrazolopyrimidine fused carbohybrid heterocycle compound library, and the preparation method thereof

The present invention relates to a carbohybrid heterocycle compound library having pyrimidine, pyrazole, and pyrazolopyrimidine fused on a carbohybrid-based molecular frame.

Efficient synthesis of L-galactose from D-galactose

Racemic protein crystallography is an emerging methodology to obtain high-resolution protein structures. Preparation of both a mirror image of protein and a mirror image of glycan is essential to apply the new methodology to glycoprotein. This article describes an efficient synthesis of L-galactose that is amirror image of D-galactose. The developed method takes only 6 steps from D-galactose without any chromatographic purification.

Synthesis of uniformly deuterated n-dodecyl-β -d-maltoside (d39 -DDM) for solubilization of membrane proteins in TROSY NMR experiments

This work reports the first synthesis of uniformly deuterated n-dodecyl-β -D-maltoside (d39-DDM). DDM is a mild non-ionic detergent often used in the extraction and purification of membrane proteins and for solubilizing them in experimental studies of their structure, dynamics and binding of ligands. We required d39-DDM for solubilizing large α-helical membrane proteins in samples for [15N-1H]TROSY (transverse relaxation-optimized spectroscopy) NMR experiments to achieve the highest sensitivity and best resolved spectra possible. Our synthesis of d39-DDM used d7-D-glucose and d25-n-dodecanol to introduce deuterium labelling into both the maltoside and dodecyl moieties, respectively. Two glucose molecules, one converted to a glycosyl acceptor with a free C4 hydroxyl group and one converted to a glycosyl donor substituted at C1 with a bromine in the α-configuration, were coupled together with an α(1 → 4) glycosidic bond to give maltose, which was then coupled with n-dodecanol by its substitution of a C1 bromine in the α-configuration to give DDM. 1H NMR spectra were used to confirm a high level of deuteration in the synthesized d39-DDM and to demonstrate its use in eliminating interfering signals from TROSY NMR spectra of a 52-kDa sugar transport protein solubilized in DDM.

Regiospecific anomerisation of acylated glycosyl azides and benzoylated disaccharides by using TiCl4

Chelation induced anomerisation is promoted when Lewis acids, such as TiCl4 or SnCl4, coordinate to the pyranose ring oxygen atom and another site, giving rise to endocyclic cleavage and isomerisation to the more stable anomer. In this research regiospecific site-directed anomerisation is demonstrated. TiCl4 (2.5equiv) was employed to induce anomerisation of 15 glycosyl azide and disaccharide substrates of low reactivity, and high yields (>75 %) and stereoselectivies (α/β>9:1) were achieved. The examples included glucopyranuronate, galactopyranuronate and mannopyranuronate as well as N-acetylated glucopyranuronate and galactopyranuronate derivatives. A disaccharide with the α1→4 linkage found in polygalacturonan was included. The use of benzoylated saccharides was found to be important in disaccharide anomerisation as attempts to isomerise related acetyl protected and 2,3-carbonate protected derivatives were not successful. Copyright