75247-31-3

Basic information

• Product Name: 2,3,4-TRI-O-ACETYL-ALPHA-L-ARABINOPYRANOSYL BROMIDE
• Synonyms: ACETOBROMO-ALPHA-L-ARABINOSE;2,3,4-TRI-O-ACETYL-ALPHA-L-ARABINOPYRANOSYL BROMIDE;Acetoromo-alpha-l-arabinose;alpha-L-Arabinopyranosyl bromide triacetate
• CAS NO: 75247-31-3
• Molecular Formula: C₁₁H₁₅BrO₇
• Molecular Weight: 339.14
• Mol File: 75247-31-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 138 °C
• Boiling Point: 337.2±42.0 °C(Predicted)
• Appearance: /
• Density: 1.51±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2,3,4-TRI-O-ACETYL-ALPHA-L-ARABINOPYRANOSYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-TRI-O-ACETYL-ALPHA-L-ARABINOPYRANOSYL BROMIDE(75247-31-3)
• EPA Substance Registry System: 2,3,4-TRI-O-ACETYL-ALPHA-L-ARABINOPYRANOSYL BROMIDE(75247-31-3)

Safety Data

• Hazardous Substances Data: 75247-31-3(Hazardous Substances Data)

Usage

General Description

2,3,4-TRI-O-ACETYL-ALPHA-L-ARABINOPYRANOSYL BROMIDE is a chemical compound with the molecular formula C13H17BrO8. It is a brominated derivative of alpha-L-arabinopyranose, a type of sugar. The compound is synthesized by reacting the sugar with acetic anhydride and a brominating reagent, resulting in the formation of the triacetate derivative. It is commonly used in organic synthesis and carbohydrate chemistry as a building block for the synthesis of more complex molecules. 2,3,4-TRI-O-ACETYL-ALPHA-L-ARABINOPYRANOSYL BROMIDE is often utilized in the development of pharmaceuticals, agrochemicals, and materials science, where the manipulation of sugar molecules plays a crucial role in the creation of new compounds with desired properties.

Upstream product

• 1233-03-0 1,2,3,4-tetra-O-acetyl-L-arabinopyranose 
• 1233-03-0 1,2,3,4-tetra-O-acetyl-α-L-arabinopyranose 
• 87-72-9 L-(+)-arabinose 
• 4258-00-8 1,2,3,4-tetra-O-acetyl-β-L-arabinopyranose 

Downstream Products

• 130999-25-6 4'-7-di-O-benzylquercet-3-yl 2,3,4-tri-O-acetyl-α-L-arabinopranoside 
• 3945-18-4 3,4-di-O-acetyl-L-arabinal 
• 518047-08-0 2'-(benzyloxy)ethyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside 
• 518047-06-8 ((2S,3R,4S,5S)-3,4,5-Triacetoxy-tetrahydro-pyran-2-yloxy)-acetic acid benzyl ester 
• 25878-56-2 Acetic acid (3S,6R)-6-methoxy-3,6-dihydro-2H-pyran-3-yl ester 
• 92122-97-9 Methyl 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-arabinopyranoside 
• 92122-95-7 Methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-arabinopyranoside 
• 92122-94-6 3,4-Di-O-benzyl-1,2-O-(1-methoxyethilidene)-β-L-arabinopyranose 
• 92122-96-8 Methyl 3,4-di-O-benzyl-α-L-arabinopyranoside 

Relevant articles and documents

Chemical synthesis of 5’-β-glycoconjugates of vitamin B6

Various 5’-β-saccharides of pyridoxine, namely the mannoside, galactoside, arabinoside, maltoside, cellobioside and glucuronide, were synthesized chemically according to KOENIGS-KNORR conditions using α4,3-O-isopropylidene pyridoxine and the respective acetobromo glycosyl donors with AgOTf (3.0 eq.) and NIS (3.0 eq.) as promoters at 0 °C. Furthermore, 5’-β-[13C6]-labeled pyridoxine glucoside (PNG) was prepared starting from [13C6]-glucose and pyridoxine. Additionally, two strategies were examined for the synthesis of 5’-β-pyridoxal glucoside (PLG).

Design and synthesis of DNA-intercalating 9-fluoren-β-O-glycosides as potential IFN-inducers, and antiviral and cytostatic agents

Novel 9-fluoren-β-O-glycosides, designed as DNA-intercalating agents in structural correlation with antiviral tilorone and anticancer anthracyclines, have been prepared with yields in β-anomers ranging between 25 and 63%. They have been screened for antiproliferative, immunostimulating and antiviral properties against HSV-1 and HSV-2 viruses. Compounds displaying significant antiviral activity against HSV-2 are acetylated 1 and deprotected 6 9-fluorenyl-O-D-arabinopyranoses, whereas 9-fluorenyl-O-D-glucopyranose 3 is the most effective on HSV-1 replication, followed by 1 and 6. The conformational properties of these compounds have been evaluated by molecular modelling techniques.

Exchange radioiodination produces inversion at C-4 of 1-(4-deoxy-4-iodo-β-D-xylopyranosyl)-2-nitroimidazole

The title compound, 3a, when exchange labeled with 125I results in three new labeled products. The major labeled product (84.1%) is 1-(4-deoxy-4-iodo-β-L-arabinopyranosyl)-2-nitroimidazole, 3b, that could result from inversion of configuration at C-4. Exchange labeling carried out under conditions of kinetic control yielded dramatically different product ratios than thermodynamic equilibrium reactions. Confirmation of these results was established by extensive 1H NMR spectral analyses. A possible mechanism is presented. Copyright