10028-44-1

Basic information

• Product Name: 1,2,3,4-TETRA-O-ACETYL-6-O-(TRIPHENYLMETHYL)-BETA-D-GLUCOPYRANOSE
• Synonyms: 1,2,3,4-TETRA-O-ACETYL-6-O-(TRIPHENYLMETHYL)-SS-D-GLUCOPYRANOSE;Nsc52915
• CAS NO: 10028-44-1
• Molecular Formula: C₃₃H₃₄O₁₀
• Molecular Weight: 590.62
• Product Categories: Sugars, Carbohydrates & Glucosides;Carbohydrates
• Mol File: 10028-44-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 633.3 °C at 760 mmHg
• Flash Point: 262.6 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 6.08E-16mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: 1,2,3,4-TETRA-O-ACETYL-6-O-(TRIPHENYLMETHYL)-BETA-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRA-O-ACETYL-6-O-(TRIPHENYLMETHYL)-BETA-D-GLUCOPYRANOSE(10028-44-1)
• EPA Substance Registry System: 1,2,3,4-TETRA-O-ACETYL-6-O-(TRIPHENYLMETHYL)-BETA-D-GLUCOPYRANOSE(10028-44-1)

Safety Data

• Hazardous Substances Data: 10028-44-1(Hazardous Substances Data)

Usage

General Description

1,2,3,4-Tetra-O-acetyl-6-O-(triphenylmethyl)-beta-D-glucopyranose is a complex chemical compound composed of a sugar molecule (glucopyranose) that has been modified with acetyl groups and a triphenylmethyl group. The acetyl groups are attached to the hydroxyl groups of the sugar, while the triphenylmethyl group is attached to the oxygen atom at the 6th position of the sugar ring. 1,2,3,4-TETRA-O-ACETYL-6-O-(TRIPHENYLMETHYL)-BETA-D-GLUCOPYRANOSE is often used as a protective group in synthetic organic chemistry to temporarily mask the reactivity of the hydroxyl groups of the sugar molecule. It can be selectively removed under specific conditions to reveal the original reactivity of the sugar molecule, making it a valuable tool in the synthesis of complex organic molecules.

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 
• 108-24-7 acetic anhydride 
• 54325-28-9 6-O-trityl-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 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

• 55286-97-0 1,2,3,6-tetra-O-acetyl-α-D-glucopyranoside 
• 13100-46-4 1,2,3,4-tetra-O-acetyl-α-D-glucopyranoside 
• 108257-54-1 1,2,3,6-tetra-O-acetyl-4-O-trityl-α-D-glucopyranose 
• 108257-52-9 1,2,3,4-tetra-O-acetyl-6-O-benzyl-α-D-glucopyranose 
• 79414-65-6 1,2,3,6-tetra-O-acetyl-4-O-benzyl-α-D-glucopyranose 

Relevant articles and documents

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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.

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.