6919-96-6

Usage

Uses

Used in Organic Synthesis:
2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL BROMIDE is used as a key intermediate in organic synthesis for the preparation of complex carbohydrates, glycoconjugates, and glycosides. Its versatile reactivity allows for the creation of a wide range of carbohydrate-based compounds with potential applications in various fields.
Used in Carbohydrate Chemistry Research:
In the field of carbohydrate chemistry, 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL BROMIDE is employed as a valuable tool for studying the structure, properties, and reactions of carbohydrates. Its ability to modify carbohydrate structures facilitates the exploration of new synthetic pathways and the development of innovative carbohydrate-based compounds.
Used in Biochemical Studies:
2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL BROMIDE is utilized in biochemical research to investigate the interactions between carbohydrates and other biomolecules, such as proteins and lipids. 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL BROMIDE aids in understanding the roles of carbohydrates in biological processes and their potential as therapeutic agents.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL BROMIDE is used as a building block for the synthesis of glycosides and other carbohydrate-based drug candidates. Its ability to form diverse carbohydrate structures contributes to the discovery of new drugs with potential therapeutic benefits.
Used in Material Science:
2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL BROMIDE is also employed in material science for the development of carbohydrate-based materials with unique properties. These materials can be used in various applications, such as sensors, catalysts, and biocompatible coatings, owing to their specific interactions with other molecules.

Upstream product

• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 67337-79-5 2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide 
• 604-68-2 α-D-glucopyranose peracetylate 
• 83-87-4 D-Mannose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 530-26-7 D-Mannose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 25878-60-8 D-galactose pentaacetate 
• 83-87-4 D-glucose pentaacetate 
• 506-96-7 Acetyl bromide 
• 10257-28-0 D-Galactose 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 

Downstream Products

• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 40437-08-9 O²,O³,O⁴,O⁶-Tetraacetyl-galactose 
• 82462-53-1 <1(R),2(R)-(2-hydroxycyclohexyl)>-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 82462-53-1 <1(S),2(S)-(2-hydroxycyclohexyl)>-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 122664-47-5 tetra-O-acetyl-β-(2,6-dimethyl-5-phenyl-4-oxo-1,4-dihydropyrimidine-1)-D-glucopyranoside 
• 76299-67-7 4-Benzyloxy-3-hydroxy-2-methylene-butyric acid (3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester 
• 79258-22-3 methyl endo/exo-2,3-O-(2-nitrobenzylidene)-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside 
• 79258-20-1 2-Nitro-benzoic acid (2R,3R,4R,5S,6S)-2-methoxy-6-methyl-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 
• 79258-20-1 methyl 2-O-(2-nitrobenzoyl)-3,4-di-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside 
• 125365-18-6 Methyl 2-O-allyl-4,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-<*>-galactopyranosyl)-α-<*>-mannopyranoside 
• 73168-12-4 1-methyl-6-(phenylmethoxy)-10-<(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy>benzo<1>benzopyrano<5,4,3-cde><1>benzopyran-5,12-dione 
• 13035-51-3 tert-butyl-(tetra-O-acetyl-β-D-glucopyranoside) 
• 84863-61-6 3,6-dibenzoyl-14-O-(tetraacetyl-β-D-glucopyranosyl)grayanotoxin III 
• 16977-78-9 2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis and anti-tumor activity of glycosyl oxadiazoles derivatives

A new series of glycosyl oxadiazoles compounds were synthesized and characterized through 1H NMR, 13C NMR, IR and HRMS. The anti-tumor activities for MDA-MB-231 of all these new compounds were screened in vitro by MTT assay. Due to the modification of gastrodin analogues, the anti-tumor activities of these 1,3,4-oxadiazoles derivatives were greatly improved. Six compounds (6c, 6d, 6i, 6j, 6k and 6l) displayed relatively higher MDA-MB-231 potency with IC50 values (0.89, 0.26, 1.35, 3.60, 0.95 and 1.08 μM) compared with the reference medicine Rosiglitazone (5.23 μM).

FA-97, a New Synthetic Caffeic Acid Phenethyl Ester Derivative, Ameliorates DSS-Induced Colitis Against Oxidative Stress by Activating Nrf2/HO-1 Pathway

Inflammatory bowel disease (IBD) is a chronic idiopathic inflammatory disorder of gastro-intestinal tract, lacking effective drug targets and medications. Caffeic acid phenethyl ester (CAPE), a phenolic constituent derived from propolis, has been reported

Enhancing cellular sulfane sulfur through β-glycosidase-activated persulfide donors: mechanistic insights and oxidative stress mitigation

Sulfane sulfur species such as persulfides and polysulfides along with hydrogen sulfide protect cells from oxidative stress and are key members of the cellular antioxidant pool. Here, we report perthiocarbamate-based prodrugs that are cleaved by β-glycosidases to produce persulfide and relatively innocuous byproducts. The β-glucosidase-activated persulfide donor enhances cellular sulfane sulfur and protects cells against lethality induced by elevated reactive oxygen species (ROS).

Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity

Tacrine is a known Acetylcholinesterase (AChE) inhibitors having hepatotoxicity as main liability associated with it. The present study aims to reduce its hepatotoxicity by synthesizing tacrine linked triazole glycoconjugates via Huisgen's [3 + 2] cycloaddition of anomeric azides and terminal acetylenes derived from tacrine. A series of triazole based glycoconjugates containing both acetylated (A-1 to A-7) and free sugar hydroxyl groups (A-8 to A-14) at the amino position of tacrine were synthesized in good yield taking aid from molecular docking studies and evaluated for their in vitro AChE inhibition activity as well as hepatotoxicity. All the hybrids were found to be non-toxic on HePG2 cell line at 200 μM (100 % cell viability) as compared to tacrine (35 % cell viability) after 24 h of incubation period. Enzyme kinetic studies carried out for one of the potent hybrids in the series A-1 (IC50 0.4 μM) revealed its mixed inhibition approach. Thus, compound A-1 can be used as principle template to further explore the mechanism of action of different targets involved in Alzheimer's disease (AD) which stands as an adequate chemical probe to be launched in an AD drug discovery program.

Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents

In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.

Synthesis of malformin-A1, C, a glycan, and an aglycon analog: Potential scaffolds for targeted cancer therapy

Improvement in therapeutic efficacy while reducing chemotherapeutic side effects remains a vital objective in synthetic design for cancer treatment. In keeping with the ethos of therapeutic development and inspired by the Warburg effect for augmenting biological activities of the malformin family of cyclic-peptide natural products, specifically anti-tumor activity, a β-glucoside of malformin C has been designed and synthesized utilizing precise glycosylation and solution phase peptide synthesis. We optimized several glycosylation procedures utilizing different donors and acceptors. The overarching goal of this study was to ensure a targeted delivery of a glyco-malformin C analog through the coupling of D-glucose moiety; selective transport via glucose transporters (GLUTs) into tumor cells, followed by hydrolysis in the tumor microenvironment releasing the active malformin C a glycon analog. Furthermore, total synthesis of malformin C was carried out with overall improved strategies avoiding unwanted side reactions thus increasing easier purification. We also report on an improved solid phase peptide synthesis protocol for malformin A1.

CuAAC mediated synthesis of cyclen cored glycodendrimers of high sugar tethers at low generation

Glycodendrimers are receiving considerable attention to mimic a number of imperative features of cell surface glycoconjugate and acquired excellent relevance to a wide domain of investigations including medicine, pharmaceutics, catalysis, nanotechnology, carbohydrate-protein interaction, and moreover in drug delivery systems. Toward this end, an expeditious, modular, and regioselective triazole-forming CuAAC click approach along with double stage convergent synthetic method was chosen to develop a variety of novel chlorine-containing cyclen cored glycodendrimers of high sugar tethers at low generation of promising therapeutic potential. We developed a novel chlorine-containing hypercore unit with 12 alkynyl functionality originated from cyclen scaffold which was confirmed by its single crystal X-ray data analysis. Further, the modular CuAAC technique was utilized to produce a variety of novel 12–sugar coated (G0) glycodendrimers 12-15 adorn with β-Glc-, β-Man-, β-Gal-, β-Lac, along with 36-galactose coated (G1) glycodendrimer 18 in good-to-high yield. The structures of the developed glycodendrimer architectures have been well elucidated by extensive spectral analysis including NMR (1H & 13CNMR), HRMS, MALDI-TOF MS, UV–Vis, IR, and SEC (Size Exclusion Chromatogram) data.

Synthesis of podophyllotoxin-glycosyl triazoles via click protocol mediated by silver (I)-N-heterocyclic carbenes and their anticancer evaluation as topoisomerase-II inhibitors

Herein we report the regioselective synthesis of podophyllotoxin-Glycosyl triazole hybrids catalysed by Ag(I)-N-heterocyclic carbene (Ag(I)-NHC) in a short reaction time (～30 min) at ambient conditions. In principle, it is the first report of Click alkyne-azide cycloaddition catalysed by Ag(I)-NHC catalyst and moreover, this new methodology yielded good results when compared with traditional CuAAC in terms of reaction time and selectivity. The synthesised compounds were further explored for in vitro anticancer activity against four human cancer cell lines Du145, HeLa, A-549, and MCF-7 and found that these synthesised compounds possess significant anticancer activity. Further, the compounds 5a and 5e were identified as promising leads due to their better activity across all cell lines than that of the standard drug etoposide. Molecular docking studies of 5a & 5e with DNA Topoisomerase-II were revealed that the free energy calculations of active compounds were in good agreement with observed IC50 values.

CHARGE VARIANT LINKERS

The present disclosure provides, inter alia, ADCs with charge variant chemical linkers useful in treating various diseases such as cancer and autoimmune disorders.

GLYCOSIDE COMPOUND AND PREPARATION METHOD THEREFOR, COMPOSITION, APPLICATION, AND INTERMEDIATE

The present invention discloses a glycoside compound represented by Formula III, and a preparation method, a composition, use and an intermediate thereof. The glycoside compound provided in the present invention has simple preparation method, can significantly increase the expression of VEGF-A mRNA, and is effective in promoting the angiogenesis. This provides a reliable guarantee for the development of drugs with pro-angiogenic activity for treating cerebral infarction cerebral stroke, myocardial infarction, and ischemic microcirculatory disturbance of lower limbs.