10028-44-1

Usage

Uses

Used in Synthetic Organic Chemistry:
1,2,3,4-TETRA-O-ACETYL-6-O-(TRIPHENYLMETHYL)-BETA-D-GLUCOPYRANOSE is used as a protective group for the hydroxyl groups of sugar molecules during the synthesis of complex organic compounds. Its application is crucial for temporarily masking the reactivity of these groups, facilitating controlled reactions and preventing unwanted side reactions. The triphenylmethyl group can be selectively removed under specific conditions, revealing the original reactivity of the sugar molecule and enabling further synthetic transformations.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2,3,4-TETRA-O-ACETYL-6-O-(TRIPHENYLMETHYL)-BETA-D-GLUCOPYRANOSE is utilized as a key intermediate in the synthesis of various pharmaceutical compounds, particularly those involving sugar-based structures. Its ability to protect and later reveal the reactivity of the sugar molecule is essential for the development of new drugs with specific therapeutic properties.
Used in Research and Development:
1,2,3,4-TETRA-O-ACETYL-6-O-(TRIPHENYLMETHYL)-BETA-D-GLUCOPYRANOSE is employed as a research tool in academic and industrial laboratories for the investigation of new synthetic pathways and the development of innovative chemical reactions. Its unique properties allow chemists to explore the reactivity of sugar molecules under various conditions, leading to a deeper understanding of organic chemistry and the discovery of new synthetic methods.

InChI:InChI=1/C33H34O10/c1-21(34)39-29-28(43-32(42-24(4)37)31(41-23(3)36)30(29)40-22(2)35)20-38-33(25-14-8-5-9-15-25,26-16-10-6-11-17-26)27-18-12-7-13-19-27/h5-19,28-32H,20H2,1-4H3/t28-,29-,30+,31-,32-/m0/s1

Upstream product

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

Downstream Products

• 13100-46-4 1,2,3,4-tetra-O-acetyl-α-D-glucopyranoside 
• 55286-97-0 1,2,3,6-tetra-O-acetyl-α-D-glucopyranoside 
• 79414-65-6 1,2,3,6-tetra-O-acetyl-4-O-benzyl-α-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 

Relevant academic research and scientific papers

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.

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.

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.

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