13100-46-4

Usage

Uses

Used in Research Applications:
2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE is used as a substrate in the study of inositol synthase, an enzyme involved in the biosynthesis of inositol. This application is crucial for understanding the enzyme's function and its role in various biological processes.
Used in Chemical Synthesis:
In the chemical industry, 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE is used for the preparation of anionic surfactants. These surfactants are important in the formulation of detergents, cleaners, and other products that require emulsifying, dispersing, or wetting properties. The acetylated glucose derivative serves as a key intermediate in the synthesis of these surfactants, contributing to their stability and effectiveness.

InChI:InChI=1/C14H20O10/c1-6(16)20-11-10(5-15)24-14(23-9(4)19)13(22-8(3)18)12(11)21-7(2)17/h10-15H,5H2,1-4H3

Upstream product

• 37074-90-1 1,2,3,4-tetra-O-acetyl-6-O-trityl-β-D-glucopyranose 
• 1600-27-7 mercury(II) diacetate 
• 56767-75-0 2,3,4-tri-O-acetyl-α-D-glucopyranosyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 108-98-5 thiophenol 
• 2280-44-6 D-Glucose 
• 492-62-6 alpha-D-glucopyranose 
• 54325-28-9 6-O-trityl-α-D-glucose 
• 54325-28-9 (2R,3R,4S,5S,6R)-6-Trityloxymethyl-tetrahydro-pyran-2,3,4,5-tetraol 
• 604-69-3 β-D-glucose pentaacetate 
• 54325-28-9 6-O-trityl-D-glucopyranose 
• 67919-36-2 1,2,3,4-tetra-O-acetyl-6-O-trityl-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 
• 492-61-5 β-D-glucose 

Downstream Products

• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 123814-34-6 O¹,O²,O³,O⁴-Tetraacetyl-O⁶-(bis-benzyloxy-phosphoryl)-β-D-glucopyranose 
• 4752-94-7 O¹,O²,O³,O⁴-tetraacetyl-O⁶-(tri-O-acetyl-2-benzoylamino-2-deoxy-β-D-glucopyranosyl)-β-D-glucopyranose 
• 71208-20-3 1,2,3,4-tetra-O-acetyl-6-O-benzoyl-β-D-glucopyranose 
• 114510-26-8 O¹,O²,O³,O⁴-Tetraacetyl-O⁶-phenylcarbamoyl-β-D-glucopyranose 
• 28154-38-3 O¹,O²,O³,O⁴-tetraacetyl-O⁶-methanesulfonyl-β-D-glucopyranose 
• 6619-10-9 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-β-D-glucopyranose 
• 108321-48-8 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose 6-diphenylphosphate 
• 56-73-5 D-glucose 6-phosphate 
• 4613-78-9 β-D-gentiobiose octaacetate 
• 32449-92-6 D-glucurono-6,3-lactone 
• 13242-55-2 2,3,4-tri-O-acetyllevoglucosan 
• 39706-70-2 O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-O-1,2,3,4-tetra-O-acetyl-β-D-glucopyranose 
• 10225-48-6 1,2,3,4-tetra-O-acetyl-6-bromo-6-deoxy-β-D-glucopyranose 

Relevant academic research and scientific papers

Selective deprotection of trityl group on carbohydrate by microflow reaction inhibiting migration of acetyl group

The trityl group is an important and useful protecting group for primary hydroxy groups on carbohydrates. However, during deprotection, neighboring acetyl groups can easily migrate to the deprotected hydroxy groups. Hence, deprotection of trityl groups was optimized using a microreactor with regard to flow rate, reagent concentration, reaction time, and substrate concentration. The optimized microflow reaction conditions inhibited migration and could be applied to large-scale reactions and other substrates.

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.

NOVEL BENZIMIDAZOLE DERIVATIVES, PREPARATION METHOD THEREOF AND USE THEREOF AS ANTI-CANCER AGENT COMPRISING THE SAME

According to the present invention, there are provided a benzimidazole carbamate-sugar compound conjugate compound represented by the following Chemical Formula 1, a preparation method thereof, and a use thereof as an anti-cancer agent: Wherein, R1, R2, R3 and X are as defined in the specification and claims.

Regio- A nd chemoselective deprotection of primary acetates by zirconium hydrides

A combination of DIBAL-H and Cp2ZrCl2 is shown to promote the regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds. Apart from providing highly valuable building blocks in only two steps from biosourced raw materials, this selective de-O-acetylation should also be strongly helpful to solve selectivity issues in organic synthesis.

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.

Biocatalytic Process Optimization for the Production of High-Added-Value 6-O-Hydroxy and 3-O-Hydroxy Glycosyl Building Blocks

A biocatalytic process to synthesize regioselective monohydroxy glycosyl building blocks has been optimized. Lipases immobilized on commercial supports were treated with water-soluble carbodiimide (EDC) at different concentrations. In the presence of cosolvents, the stability of lipases adsorbed on octyl-Sepharose improved after the EDC modification. The new Candida rugosa lipase (CRL) modified heterogeneous biocatalysts were tested in the production of 6-OH hydroxyl-tetraacetyl glucose by a regioselective mono-deacetylation in aqueous media. Improvements in activity and excellent regioselectivity were obtained for octyl-CRL-EDC10mM preparation, with 95 % isolated yield of product on a multimilligram scale. We also observed excellent recyclability. The C-6 alcohol was transformed to a C-3 alcohol by chemical migration, and both compounds were transformed successfully in the corresponding new trichloroacetimidyl glucoderivatives. Modified CRL biocatalysts were also tested in the selective deprotection of peracetylated thymidine, and octyl-CRL-EDC10mM showed excellent specificity and improved regioselectivity to produce 3-hydroxy-5-acetyl-thymidine, a precursor of azidethymidine (AZT), in 95 % yield. The new Rhizomucor miehei lipase (RML)-modified heterogeneous biocatalysts showed excellent regioselectivity and recyclability in the 3-OH mono-deprotection of peracetylated lactal.

SUGAR CONTAINING, AMPHIPHILIC COPOLYMERS

Disclosed herein are polymers made from at least one monomer of formulae (I), (II), (III), and (IV), in combination with a monomer of formula (V) that may be used in pharmaceutical formulations. These polymers comprise a hydrocarbon backbone and are made from monomers that contain at least one carbon-carbon double bond. Methods of making these polymers are also disclosed.

Glycopolymer self-assemblies with gold(I) complexed to the core as a delivery system for auranofin

A new glycomonomer 1 containing a thioacetate group in the anomeric position and mimicking the thiosugar ligand of the gold-based drug auranofin was designed and synthesized in four steps from d-glucose. Both CPADB-mediated homopolymerization and chain extension of a hydrophilic poly(OEGMEMA) macroRAFT agent were well-controlled with dispersities (D) below 1.2, highlighting the suitability of thioacetate as a thiol protecting group in RAFT polymerization. Using the homopolymer as a test system, the thioacetate protective groups were selectively removed using hydrazine acetate, and AuPEt3Cl was subsequently complexed to the exposed thiols to generate a polymeric auranofin analogue with 52% complexation efficiency. Extension of this successful procedure to three block copolymers with differing hydrophobic block lengths, poly(OEGMEMA)34-b-poly(1)47, poly(F-OEGMEMA)32-b-poly(1)27, and poly(F-OEGMEMA)32-b-poly(1)7 (where F in the last two indicates the incorporation of 2 wt % fluorescein methacrylate into the hydrophilic block), produced well-defined complexed block copolymers with complexation efficiencies comparable to that of the homopolymer. Self-assembly of the longest complexed polymer poly(OEGMEMA)34-b-poly(1-AuPEt3)47 generated spherical micelles with a hydrodynamic diameter Dh of 28 nm when prepared by slow water addition to a dilute DMF solution. The IC50 value against OVCAR-3 cells in a serum-free media was 44 μM on a gold concentration basis, compared to 0.3 μM for auranofin itself. The two shorter fluorescent complexed block copolymers formed spherical micelles with Dh 23 and 9 nm, respectively, and proved more cytotoxic than their longer counterpart, both displaying IC50 values of 13.5 μM. The addition of serum to the cell growth medium reduced the cytotoxicity of auranofin by a factor of 3.6 but had a less marked effect on the fluorescent micellar systems, reducing their toxicities by between 2.4 and 2.8 times. These micellar systems therefore show less susceptibility to deactivation by serum proteins (which is the primary limitation to auranofins in vivo effectiveness) than the free auranofin, suggesting some protective benefit offered by the hydrophilic shell. Fluorescence microscopy of the two fluorescent systems revealed an accumulation in the lysosomes of the OVCAR-3 cells. The cytotoxicity mechanism may therefore differ from that of auranofin, which is known to interact with mitochondrial proteins.