113889-50-2

Basic information

• Product Name: 2,3,4-TRI-O-ACETYL-ALPHA-D-ARABINOPYRANOSYL BROMIDE
• Synonyms: ACETOBROMO-ALPHA-D-ARABINOSE;1-BROMO-2,3,4-TRI-O-ACETYL-D-ARABINOPYRANOSE;2,3,4-TRI-O-ACETYL-ALPHA-D-ARABINOPYRANOSYL BROMIDE;2,3,4-TRI-O-ACETYL-D-ARABINOPYRANOSYL BROMIDE;3,4,6-TRI-O-ACETYL-BETA-L-IDOPYRANOSE 1,2-(METHYLORTHOACETATE);alpha-D-Arabinopyranosyl bromide triacetate;2,3,4-Tri-O-acetyl-D-arabinopyranosyl bromide - Stabilised with 2% CaCO3
• CAS NO: 113889-50-2
• Molecular Formula: C₁₁H₁₅BrO₇
• Molecular Weight: 339.14
• Mol File: 113889-50-2.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,4-TRI-O-ACETYL-ALPHA-D-ARABINOPYRANOSYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-TRI-O-ACETYL-ALPHA-D-ARABINOPYRANOSYL BROMIDE(113889-50-2)
• EPA Substance Registry System: 2,3,4-TRI-O-ACETYL-ALPHA-D-ARABINOPYRANOSYL BROMIDE(113889-50-2)

Safety Data

• Hazardous Substances Data: 113889-50-2(Hazardous Substances Data)

Usage

General Description

2,3,4-TRI-O-ACETYL-ALPHA-D-ARABINOPYRANOSYL BROMIDE is a chemical compound with the molecular formula C11H15BrO8. It is a derivative of alpha-D-arabinopyranosyl bromide and is commonly used in organic synthesis and chemical research. 2,3,4-TRI-O-ACETYL-ALPHA-D-ARABINOPYRANOSYL BROMIDE is a brominated sugar derivative and is often used as a reactant in the synthesis of other chemical compounds. It is a white to off-white solid in appearance and is soluble in various organic solvents. 2,3,4-TRI-O-ACETYL-ALPHA-D-ARABINOPYRANOSYL BROMIDE is mainly used as a building block in the preparation of pharmaceuticals, agrochemicals, and other biologically active compounds.

Upstream product

• 10369-25-2 2,3,4-tri-O-acetyl-D-arabinopyranose 
• 108646-05-5 (3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 
• 28697-53-2 D-arabinopyranose 
• 10323-20-3 D-Arabinose 

Downstream Products

• 3152-43-0 3,4-di-O-acetyl-D-xylal 
• 62414-75-9 2,3,4-tri-O-acetyl-α-D-arabinopyranosyl isotyhiocyanate 
• 403822-05-9 4-(2',3',4'-tri-O-acetyl-β-D-arabinopyranosyloxy)benzaldehyde 
• 403822-06-0 3-(2',3',4'-tri-O-acetyl-β-D-arabinopyranosyloxy)benzaldehyde 
• 391928-90-8 (2S)-2-benzyloxy-2H-pyran-3-(6H)-one 
• 476487-84-0 (3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-methano-1H-2-benzopyran-4(3H)-one 
• 581095-83-2 (3S,4aS,5R,8S,8aR)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-methano-1H-2-benzopyran-4(3H)-one 
• 476487-90-8 (3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-ethano-1H-2-benzopyran-4(3H)-one 
• 25878-56-2 Acetic acid (3S,6R)-6-methoxy-3,6-dihydro-2H-pyran-3-yl ester 
• 3152-43-0 3,4-di-O-acetyl-D-arabinal 

Relevant articles and documents

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.

Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors

Lysophosphatidylserine (LysoPS), an endogenous ligand of G protein-coupled receptors, consists of l-serine, glycerol, and fatty acid moieties connected by phosphodiester and ester linkages, respectively. An ester linkage of phosphatidylserine can be hydrolyzed at the 1-position or at the 2-position to give 2-acyl lysophospholipid or 1-acyl lysophospholipid, respectively. 2-Acyl lysophospholipid is in nonenzymatic equilibrium with 1-acyl lysophospholipid in vivo. On the other hand, 3-acyl lysophospholipid is not found, at least in mammals, raising the question of whether the reason for this might be that the 3-acyl isomer lacks the biological activities of the other isomers. Here, to test this idea, we designed and synthesized a series of new 3-acyl lysophospholipids. Structure-activity relationship studies of more than 100 "glycol surrogate"derivatives led to the identification of potent and selective agonists for LysoPS receptors GPR34 and P2Y10. Thus, the non-natural 3-acyl compounds are indeed active and appear to be biologically orthogonal with respect to the physiologically relevant 1-and 2-acyl lysophospholipids.

Synthesis of C3-Neoglycosides of digoxigenin and their anticancer activities

Cardiac glycosides exhibit significant anticancer effects and the glycosyl substitution at C3 position of digoxigenin is pivotal for their biological activity. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and explore more potent anticancer agents, a series of C3-O-neoglycosides and C3-MeON-neoglycosides of digoxigenin were synthesized by the Koenigs-Knorr and neoglycosylation method, respectively. In addition, digoxigenin bisdigitoxoside and monodigitoxoside were prepared from digoxin by sodium periodate (NaIO4) oxidation and 6-aminocaproic acid hydrolysis. The SAR analysis revealed that C3-O-neoglycosides of digoxigenin exhibited stronger cytotoxicity and induction of Nur77 expression of tumor cells than C3-MeON-neoglycosides. Also, 3β-O-glycosides exhibited stronger anticancer effects than 3α-O-glycosides. Among them, 3β-O-(β-L-fucopyranosyl)-digoxigenin (3i) showed the highest activity on induction of Nur77 expression and translocation from the nucleus to cytoplasm, leading to cancer cell apoptosis.