40591-65-9

Usage

Uses

Used in Organic Synthesis:
2-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL)-2-THIOPSEUDOUREA HYDROBROMIDE is used as a synthetic intermediate for the development of complex organic molecules. Its application in organic synthesis is due to its ability to serve as a versatile building block, which can be further modified or functionalized to create a wide range of compounds with diverse properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL)-2-THIOPSEUDOUREA HYDROBROMIDE is used as a key component in the synthesis of potential drug candidates. Its unique structure allows for the development of novel therapeutic agents that can target specific biological pathways or receptors, potentially leading to the creation of more effective and targeted treatments for various diseases and conditions.
Used in Chemical Research:
2-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL)-2-THIOPSEUDOUREA HYDROBROMIDE is also used as a research tool in chemical laboratories. Its distinctive chemical properties make it an interesting subject for studying various aspects of organic chemistry, such as reaction mechanisms, stereochemistry, and the development of new synthetic methods.

Upstream product

• 17356-08-0 thiourea 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-68-2 α-D-glucopyranose peracetylate 
• 604-69-3 β-D-glucose pentaacetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 4163-60-4 β-D-galactose peracetate 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 61303-35-3 2,3,4,6-tetra-O-acetyl-α-L mannopyranosyl bromide 
• 25878-60-8 D-galactose pentaacetate 
• 10257-28-0 D-Galactose 
• 108-24-7 acetic anhydride 
• 83-87-4 D-glucose pentaacetate 
• 2280-44-6 D-Glucose 

Downstream Products

• 13350-45-3 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 6806-56-0 O²,O³,O⁴,O⁶,S-Pentaacetyl-1-thio-β-D-glucopyranose 
• 68703-54-8 2,3,4,6-tetra-O-acetyl-1-S-trityl-1-thio-β-D-glucopyranose 
• 3254-07-7 2,4-Dinitrophenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 5505-45-3 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 6612-63-1 benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 64978-30-9 S-allyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 85618-21-9 octyl-beta-D-thioglucopyranoside 
• 85618-19-5 n-hexyl 1-thio-β-D-glucopyranoside 
• 85618-20-8 heptyl-β-D-thioglucopyranoside 
• 98854-15-0 n-nonyl-β-D-thioglucopyranoside 
• 98854-16-1 n-Decyl 1-thio-β-D-glucopyranoside 
• 151123-91-0 methyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Large-scale synthesis of thio-glucose-conjugated chlorin E6 for photodynamic therapy

Chlorin e6 is a heterocycle exhibiting spectral absorption in the 600-700 nm wavelength range used for photodynamic therapy (PDT). Herein, a sugar-conjugated chlorin e6 derivative was synthesized on a large scale. An alkyl spacer was fabricated by controlling the alkoxylation conditions between the thio-sugar and chlorin e6 and thio-glucose-conjugated chlorin e6 was successfully synthesized.

8-Hydroxyquinoline glycoconjugates containing sulfur at the sugar anomeric position—synthesis and preliminary evaluation of their cytotoxicity

One of the main factors limiting the effectiveness of many drugs is the difficulty of their delivery to their target site in the cell and achieving the desired therapeutic dose. Moreover, the accumulation of the drug in healthy tissue can lead to serious side effects. The way to improve the selectivity of a drug to the cancer cells seems to be its conjugation with a sugar molecule, which should facilitate its selective transport through GLUT transporters (glucose transporters), whose overexpression is seen in some types of cancer. This was the idea behind the synthesis of 8-hydroxyquinoline (8-HQ) derivative glycoconjugates, for which 1-thiosugar derivatives were used as sugar moiety donors. It was expected that the introduction of a sulfur atom instead of an oxygen atom into the anomeric position of the sugar would increase the stability of the obtained glycoconjugates against untimely hydrolytic cleavage. The anticancer activity of new compounds was determined based on the results of the MTT cytotoxicity tests. Because of the assumption that the activity of this type of compounds was based on metal ion chelation, the effect of the addition of copper ions on cell proliferation was tested for some of them. It turned out that cancer cells treated with glycoconjugates in the presence of Cu2+ had a much slower growth rate compared to cells treated with free glycoconjugates in the absence of copper. The highest cytotoxic activity of the compounds was observed against the MCF-7 cell line.

POLYMER FOR DELIVERY OF BIOLOGICALLY ACTIVE MATERIALS

The present invention mainly relates to a polymer for delivery of biologically active materials, a complex and a method of synthesis thereof. The polymer comprises a poly(ethylene imine) and at least one monomer, each monomer comprising a modified sugar moiety, preferably galactose, comprising a sulphur atom or a nitrogen atom and a chemical moiety comprising a terminal epoxide for linking the polyethylene imine to the monomer, wherein the sulphur atom or the nitrogen atom links the modified sugar moiety to the chemical moiety. The biologically active material is preferably a gene, siRNA, mRNA, or plasmid DNA. Further disclosed is the medical use of said complex in treating a disease caused by a genetic disorder, for example cancer.

Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics

Here, we report on the first combined one-pot use of the two so-called "click reactions": The thiol-ene coupling and the copper-catalyzed alkyne-azide cycloaddition. These reactions were employed in an alternating and one-pot fashion to combine appropriately functionalized monomeric carbohydrate building blocks to create mimics of trisaccharides and tetrasaccharides as single anomers, with only minimal purification necessary. The deprotected oligosaccharide mimics were found to bind both plant lectins and human galectin-3.

Improved Synthesis of Glucosinolates

Herein we describe an improved synthesis of glucosinolates, in which the quantity and cost of materials have been reduced by approximately an order of magnitude compared to typical literature procedures. This allowed us to produce multiple glucosinolates in 10-25 gram batches using vessel sizes no larger than 0.5 litres.

A preparation method of the isothiourea hydrobromide

The invention relates to the sugar compound field, and concretely relates to a synthesis method of isothiourea dihydrobromide. The method comprises the following steps: adding acetic anhydride and a catalyst at room temperature, adding D-galactose, adding an acetic acid solution of hydrogen bromide after a reaction, adding the obtained reaction solution to thiourea and an acetonitrile solution with the temperature of 60-65DEG C in a dropwise manner, carrying out a temperature control reaction, post-processing to obtain 2-S-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranose)-2-isothiourea dihydrobromide with the purity of above 99%. The above compound is synthesized through the one-step reaction method, and the method has the advantages of simple operation, easily available raw materials, and operation cost and material saving.

Electron-catalyzed radical perfluoroalkylation of organic sulfides: The serendipitous use of the TMEDA/I2 complex as a radical initiator

Radical initiation for the perfluoroalkylation reaction of sulfides has been performed using the complex [(TMEDA)I·I3] and visible light. This methodology bypasses the use of metal(organo)catalysts where the complex [(TMEDA)I·I3] acts as a good electron donor/reductant radical initiating agent. Biologically relevant sulfides are easily substituted with RF moieties employing a mild and environmentally benign radical strategy starting from readily available RFI.

Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature

A general and efficient protocol for the palladium-catalyzed functionalization of mono- and polyglycosyl thiols by using the palladacycle precatalyst G3-XantPhos was developed. The C-S bond-forming reaction was achieved rapidly at room temperature with various functionalized (hetero)aryl-, alkenyl-, and alkynyl halides. The functional group tolerance on the electrophilic partner is typically high and anomer selectivities of thioglycosides are high in all cases studied. New sulfur nucleophiles such as thiophenols, alkythiols, and thioaminoacids (cysteine) were also successfully coupled to lead to the most general and practical method yet reported for the functionalization of thiols.

Synthesis and characterization of novel cationic lipids derived from thio galactose

Two double chain cationic lipids QAS Cn -2-S (n = 12, 14) derived from thio galactose and carbamate-linkage tertiary amine were synthesized and their structures were confirmed by MS, TOF-MS, 1H NMR and 13C NMR. The QAS C12-2-S revealed superior surface activity compared with QAS C14-2-S with lower CMC and γCMC. Though Lipo C12-2-S displayed large average particle-size with high polydispersity, positive charged Lipo Cn -2-S can be combined with the negative charged DNA, also negatively stained TEM images confirmed the formation of vesicles. All the above prove that the Lipo Cn -2-S is helpful for gene transfection.

Preparation and X-ray analysis of potassium (2,3-dichlorophenyl) glucosinolate

There has been much interest in obtaining crystals for crystallographic analysis of biologically active glucosinolates. Crystals of potassium (2,3-dichlorophenyl)glucosinolate were obtained as a dual solvate, containing one methanol and one ethanol molecule of crystallization, K+ C 13H14Cl2NO9S2 - CH3OH C2H5OH. The three-dimensional polymeric network consists of chains containing the potassium ions coordinated and bridged by sugar O atoms, which run parallel to the a axis and are further crosslinked through the sugar molecules. The channels of this network are occupied by the dichlorophenyl substituents and the ethanol and methanol solvent molecules. The structure of the S-(2,3,4,6-tetra-O-acetyl- β-d-glucopyranosyl)-2,3-dichlorophenylacetothiohydroxymate, C 21H23Cl2NO10S, precursor has also been determined and the β-configuration and Z isomer of the thiohydroximate substituent is confirmed.