37074-90-1

Usage

Uses

Used in Organic Synthesis:
6-TRITYL-1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCOSE is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows for the creation of a wide range of molecules, making it a valuable component in the field of organic chemistry.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 6-TRITYL-1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCOSE is used as a building block for the synthesis of new drugs. Its versatile chemical properties enable the development of innovative therapeutic agents with potential applications in treating various diseases and conditions.
Used in Natural Product Synthesis:
6-TRITYL-1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCOSE is also employed in the synthesis of natural products, which are compounds derived from living organisms. Its role in this process is to facilitate the creation of complex natural molecules with potential medicinal properties.
Used in Chemical Research and Development:
Due to its unique reactivity, 6-TRITYL-1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCOSE is utilized in chemical research and development to explore new molecular structures and reactions. This contributes to the advancement of chemical knowledge and the discovery of novel applications for 6-TRITYL-1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCOSE.

Upstream product

• 50-99-7 D-glucose 
• 596-43-0 bromo-triphenyl-methane 
• 76-83-5 trityl chloride 
• 54325-28-9 6-O-trityl-α-D-glucose 
• 108-24-7 acetic anhydride 
• 54325-28-9 (2R,3R,4S,5S,6R)-6-Trityloxymethyl-tetrahydro-pyran-2,3,4,5-tetraol 
• 2280-44-6 D-Glucose 
• 492-62-6 alpha-D-glucopyranose 
• 54325-28-9 6-O-trityl-D-glucopyranose 

Downstream Products

• 13242-55-2 2,3,4-tri-O-acetyllevoglucosan 
• 13100-46-4 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose 
• 4613-78-9 β-D-gentiobiose octaacetate 
• 14877-92-0 1,2,3,4-tetra-O-acetyl-6-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-β-D-glucopyranose 
• 124595-23-9 phenyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside 
• 80768-04-3 1,2,3,4-tetra-O-acetyl-6-O-(1,3,4,6-tetra-O-benzoyl-α-D-fructofuranosyl)-β-D-glucopyranose 
• 5239-09-8 Neryl 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-6-O-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside 
• 27086-15-3 1,2,3,6-tetra-O-acetyl-β-D-glucopyranose 
• 324047-51-0 1,2,3,4-tetra-O-acetyl-6-O-[4-(10-undecenyloxy)benzoyl]-β-D-glucose 
• 10225-48-6 1,2,3,4-tetra-O-acetyl-6-bromo-6-deoxy-β-D-glucopyranose 
• 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 
• 108257-55-2 1,2,3,4-tetra-O-acetyl-6-O-benzyl-β-D-glucopyranose 
• 26184-96-3 rutinose 

Relevant academic research and scientific papers

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.

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.

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.

Design, synthesis, and biological evaluation of novel carbohydrate-based sulfamates as carbonic anhydrase inhibitors

Carbonic anhydrases (CAs) IX and XII are enzymes with newly validated potential for the development of personalized, first-in-class cancer chemotherapies. Here we present the design and synthesis of novel carbohydrate-based CA inhibitors, several of which were very efficient inhibitors (Ki10 nM) with good selectivity for cancer-associated CA isozymes over off-target CA isozymes. All inhibitors comprised a carbohydrate core with one hydroxyl group derivatized as a sulfamate. Five different carbohydrates were chosen to present a selection of molecular shapes with subtle stereochemical differences to the CA enzymes active site. Variable modifications of the remaining sugar hydroxyl groups were incorporated to provide an incremental coverage of chemical property parameters that are associated with biopharmaceutical performance. All sulfamate inhibitors displayed ligand efficiencies that are consistent with those reported for good drug lead candidates.

Kinetic analysis of β-phosphoglucomutase and its inhibition by magnesium fluoride

The isomerization of β-glucose-1 -phosphate (βG1 P) to β-glucose-6-phosphate (G6P) catalyzed by β-phosphoglucomutase (βPGM) has been examined using steady- and presteady-state kinetic analysis. In the presence of low concentrations of β-glucose-1,6- bisphosphate (βG16BP), the reaction proceeds through a Ping Pong Bi Bi mechanism with substrate inhibition (K cat = 65 s -1 , K βG1P = 15 μM, K βG1P = 0.7 μM, K i = 122 μM). If αG16BP is used as a cofactor, more complex kinetic behavior is observed, but the nonlinear progress curves canbe fit to reveal further catalytic parameters (k cat = 74 s-1 , K βG1P = 15 μM, K βG16BP = 0.8 μM, K i = 122 μM, K αG16BP = 91μM for productive binding, K αG16BP = 21 μM for unproductive binding). These data reveal that variations in the substrate structure affect transition-state affinity (approximately 140 000-fold in terms of rate acceleration) substantially more than ground-state binding (110-fold in terms of binding affinity). When fluoride and magnesium ions are present, time-dependent inhibition of the βPGM is observed. The concentration dependence of the parameters obtained from fitting these progress curves shows that a βG1 P-MgF 3- βPGM inhibitory complex is formed under the reaction conditions. The overall stability constant for this complex is approximately 2 × 10 -16 M 5 and suggests an affinity of the MgF 3 - moiety to this transition-state analogue (TSA) of ≤70 nM. The detailed kinetic analysis shows how a special type of TSA that does not exist in solution is assembled in the active site of an enzyme. Further experiments show that under the conditions of previous structural studies, phosphorylated glucose only persists when bound to the enzyme as the TSA. The preference for TSA formation when fluoride is present, and the hydrolysisof substrates when it is not, rules out the formation of a stable penta valent phosphorane intermediate in the active site of βPGM.

Degradable polymer and process for production thereof

In one embodiment of the present invention, a degradable polymer having a peroxide bond therein is disclosed. The degradable polymer can be utilized in the fields of medicals or medical materials, can be applied to a DDS or gene delivery system, and can be used as a novel polymeric material or environmentally-friendly material. A polyperoxide, which is an alternating copolymer, has in a side chain thereof, a functional group (which is a substituent comprising a therapeutic molecule), a water-soluble substituent, or a biodegradable substituent.

1,2,3,4-Tetra-O-acetyl-β-D-gluco-pyranuronic acid monohydrate at 120 K and anhydrous 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose at 292 K

The structure of the title acid as the monohydrate, C14H 18O11·H2O, displays hydrogen bonding which connects the molecules in layers parallel to (101). In the anhydrous glucopyranose, C14H20O10, only chain connectivity is attained but, due to disorder of the OH group, only partially and in two modes, one less favoured than the other. This provides incomplete connectivity between molecules in corrugated layers parallel to (010).

Self-assembly of β-glucosidase and D-glucose-tethering zeolite crystals into fibrous aggregates

β-Glucosidase and D-glucose-tethering micrometer-sized zeolite crystals self-assemble into thin (2-20 μm) and very long (>1 cm) fibrous aggregates in water. The process proceeds at a faster rate in a buffer solution of pH 4.8 at which the enzymatic activity is highest. The zeolite and enzyme remain intact within the fibrous material. Furthermore, the enzymatic activity of β-glucosidase is preserved even after they are kept in water for more than 6 months at room temperature. With the zeolite to enzyme weight ratio of 5, all the zeolite crystals are buried within the round fibrils which consist of either a single strand or helical double strands. Upon increasing the ratio to 10, clusters of unburied zeolite crystals appear on the exterior of the fibrils, while narrow flat fibers with smooth surfaces are formed upon decreasing the ratio to 2.5. The process is proposed to initiate by the tight binding between the zeolite-bound D-glucose moieties and β-glucosidase followed by crystallization of the enzyme over the zeolite-bound enzyme monolayer. This report thus reveals a novel behavior of β-glucosidase and demonstrates an unprecedented phenomenon that an enzyme and its substrate-tethering inorganic crystals self-assemble into structured aggregates.

Syntheses and 1H- and 13C-Nuclear Magnetic Resonance Spectra of All Positional Isomers of Tetra-O-acetyl-D-glucopyranoses, and Their Monobenzyl and Monotrityl Derivatives

All the isomers of the tetra-O-acetyl-D-glucopyranoses, and their monobenzyl and monotrityl derivatives were synthesized and systematic 1H- and 13C-nuclear magnetic resonance (1H- and 13C-NMR) studies were carried out.Complete assignments of the 1H- and 13C-NMR signals were achieved by 1H- and 13C-decoupling techniques and by the use of a shift reagent and changes of solvents.Moreover, when necessary, 1H- and 13C-shift-correlated 2D NMR spectroscopy at higher frequency (Bruker AM 400) was applied.The shifts on deacetylation, benzylation, and tritylation were estimated on the basis of the 1H- and 13C-chemical shifts of these compounds, and the effects of deacetylation and benzyl- or trityl-substitution are discussed.Keywords - tetra-O-acetyl-D-glucopyranose; monobenzyl tetra-O-acetyl-D-glucopyranose; monotrityl tetra-O-acetyl-D-glucopyranose; 1H-NMR; 13C-NMR; deacetylation shift; benzylation shift; tritylation shift