6919-96-6

Basic information

• Product Name: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL BROMIDE
• Synonyms: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL BROMIDE;2,3,4,6-TETRA-O-ACETYL-SS-D-GLUCOPYRANOSYL BROMIDE;1-Bromo-1-deoxy-β-D-glucopyranose tetraacetate;1-Bromo-2-O,3-O,4-O,6-O-tetraacetyl-1-deoxy-β-D-glucopyranose;1-Deoxy-1-bromo-β-D-glucopyranose 2,3,4,6-tetraacetate;2-O,3-O,4-O,6-O-Tetraacetyl-β-D-glucopyranosyl bromide
• CAS NO: 6919-96-6
• Molecular Formula: C₁₄H₁₉BrO₉
• Molecular Weight: 411.19926
• Mol File: 6919-96-6.mol
• Article Data: 140

Chemical Properties

• Melting Point: 88-89 °C
• Boiling Point: 412.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.49±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL BROMIDE(6919-96-6)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL BROMIDE(6919-96-6)

Safety Data

• Hazardous Substances Data: 6919-96-6(Hazardous Substances Data)

Usage

General Description

2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl bromide is a chemical compound that is commonly used in organic synthesis and as a building block for the preparation of various glycosides. It is a derivative of beta-D-glucose and contains four acetyl groups attached to the glucose molecule. 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL BROMIDE is often used in the synthesis of complex carbohydrates, glycoconjugates, and glycosides for various biological and pharmacological studies. It is important in the field of carbohydrate chemistry and biochemistry due to its ability to modify and manipulate the structure of carbohydrates for further research and applications.

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 
• 83-87-4 D-glucose pentaacetate 
• 5531-53-3 Penta-O-acetyl-galactopyranose 
• 10035-10-6 hydrogen bromide 
• 23661-29-2 phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-glucopyranoside 
• 492-61-5 β-D-glucose 
• 108-24-7 acetic anhydride 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 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 
• 2280-44-6 D-Glucose 
• 506-96-7 Acetyl bromide 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 

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 
• 96468-95-0 5-benzylidene-2-[phenyl-(tetra-O-acetyl-ξ-D-glucopyranosyl)-amino]-thiazol-4-one 
• 96553-99-0 5-benzylidene-3-(tetra-O-acetyl-ξ-D-glucopyranosyl)-2-thioxo-thiazolidin-4-one 
• 97074-54-9 5-(4-methoxy-benzylidene)-3-(tetra-O-acetyl-ξ-D-glucopyranosyl)-2-thioxo-thiazolidin-4-one 
• 58459-24-8 5-phenyl-1,3,4-thiadiazol-2-yl 2,3,4,6,-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 79258-27-8 methyl 3,4-O-endo-(2-nitrobenzylidene)-2-O-(tetra-O-acetyl-β-D-glucopyranosyl)-α-L-fucopyranoside 
• 79258-27-8 methyl 3,4-O-exo-(2-nitrobenzylidene)-2-O-(tetra-O-acetyl-β-D-glucopyranosyl)-α-L-fucopyranoside 
• 915-05-9 stigmast-5-en-3-yl acetate 
• 25694-37-5 di-β-sitosteryl ether 
• 66252-73-1 β-sitosteryl bromide 
• 79897-80-6 24-(R)-ethylcholesta-3,5-diene 
• 66252-74-2 β-sitosteryl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 4282-00-2 stigmast-5-en-3β-yl-(tetra-O-acetyl-β-D-glucopyranoside) 

Relevant articles and documents

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).

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).

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.

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.