7473-42-9

Usage

Uses

Used in Pharmaceutical Industry:
METHYL-2,3,5-TRI-O-BENZOYL-A-D-ARABINOFURANOSIDE is used as a key intermediate in the synthesis of α-AZA and β-AZA, which are potential markers for tissue hypoxia. These markers can be employed in the development of diagnostic tools and therapeutic strategies for conditions associated with tissue hypoxia, such as cancer and cardiovascular diseases.
Used in Research and Development:
In the field of research and development, METHYL-2,3,5-TRI-O-BENZOYL-A-D-ARABINOFURANOSIDE is utilized for the synthesis of novel compounds with potential applications in various areas of medicine and biology. Its unique chemical properties make it a valuable building block for the development of new drugs and diagnostic agents.
Chemical Properties:
METHYL-2,3,5-TRI-O-BENZOYL-A-D-ARABINOFURANOSIDE is a white solid with distinct chemical properties that make it suitable for use in the synthesis of various biologically active molecules. Its structure and reactivity contribute to its versatility in chemical reactions, allowing for the creation of a wide range of compounds with potential applications in the pharmaceutical and biotechnology industries.

InChI:InChI=1/C27H24O8/c1-31-27-23(35-26(30)20-15-9-4-10-16-20)22(34-25(29)19-13-7-3-8-14-19)21(33-27)17-32-24(28)18-11-5-2-6-12-18/h2-16,21-23,27H,17H2,1H3

Upstream product

• 67-56-1 methanol 
• 10323-20-3 D-Arabinose 
• 98-88-4 benzoyl chloride 
• 70051-90-0 tri-O-benzoyl-β-D-arabinofuranosyl bromide 
• 4348-68-9 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl bromide 
• 56607-40-0 methyl D-arabinofuranoside 
• 79083-42-4 methyl D-arabinofuranoside 
• 25545-03-3 β-D-arabinofuranose 
• 532-20-7 D-arabinofuranose 
• 28697-53-2 D-arabinopyranose 
• 1824-96-0 Methyl α-lyxofuranoside 

Downstream Products

• 4348-68-9 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl bromide 
• 502761-66-2 C₁₃H₁₆O₆C₁₄H₈O₂ 
• 57236-69-8 (3S,4R,5R)-2-acetoxy-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate 
• 59599-14-3 2,3,5-tetra-O-benzoyl-α-D-arabinofuranosyl chloride 
• 189324-80-9 (2R,3R,4S,5S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-tetrahydro-furan 
• 1187662-62-9 p-methoxyphenyl 2,3,5-tri-O-benzoyl-1-thio-α-D-arabinofuranoside 
• 1187662-65-2 p-methoxybenzyl 2,3,5-tri-O-benzoyl-1-thio-α-D-arabinofuranoside 
• 1187662-64-1 p-nitrophenyl 2,3,5-tri-O-benzoyl-1-thio-α-D-arabinofuranoside 
• 1379681-51-2 3,5-di-O-benzoyl-1,2-bis-O-(chloroacetyl)-D-arabinofuranose 
• 1379681-41-0 3,5-di-O-benzoyl-1,2-bis-O-(chloroacetyl)-D-arabinofuranose 
• 76612-55-0 1,2-di-O-acetyl-3,5-di-O-benzoyl-D-arabinofuranose 
• 1379681-42-1 phenyl 2-O-acetyl-3,5-di-O-benzoyl-1-thio-α-D-arabinofuranoside 
• 1379681-43-2 phenyl 3,5-di-O-benzoyl-1-thio-α-D-arabinofuranoside 
• 1431370-34-1 3,5-di-O-benzoyl-β-D-arabinofuranoside-prop-2-ynyl-1,2-orthobenzoate 

Relevant academic research and scientific papers

Preparation of the tri-arabino di-mycolate fragment of mycobacterial arabinogalactan from defined synthetic mycolic acids

An efficient synthetic approach to tri-arabino di-mycolates, using structurally defined synthetic α-, keto and methoxy mycolic acids is described.

Automated solid phase synthesis of oligoarabinofuranosides

Automated solid phase synthesis enables rapid access to the linear and branched arabinofuranoside oligosaccharides. A simple purification step is sufficient to provide the conjugation ready oligosaccharides in good yield.

Facile synthesis of β- And α-arabinofuranosides and application to cell wall motifs of M. tuberculosis

Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.

Ready preparation of furanosyl n-pentenyl orthoesters from corresponding methyl furanosides

The 3,5-di-O-benzoyl n-pentenyl orthoesters of the four pentofuranoses have been prepared. The first key intermediate in each case is the methyl pentofuranoside(s), and a user-friendly procedure for the preparation of each, based on the Callam-Lowary precedent, is described, whereby formation of the crucial α/β anomeric mixture is optimized. The mixture is used directly to prepare the corresponding perbenzoylated pentofuranosyl bromide(s) and then the title compounds.

A one-pot synthesis of 1-α- and 1-β-d-arabinofuranosyl-2- nitroimidazoles: Synthons to the markers of tumor hypoxia

1-α- and 1-β-D-Arabinofuranosyl-2-nitroimidazole (α-AZA and β-AZ A) are synthons for a number of potential markers of tissue hypoxia. A one pot synthesis in which 2-nitroimidazole is coupled with a mixture of α-and β-1-O-acetyl-2,3,5-tri-O-benzoyl-D-arabi

Synthesis and antiviral properties of arabino and ribonucleosides of 1,3-dideazaadenine, 4-nitro-1,3-dideazapurine and diketopiperazine

Different arabinosides and ribosides, viz. Ara-DDA or 9(1-β-D- arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-β-D- arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or 1(1-β-D- arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-β-D-

The synthesis and radiolabeling of novel markers of tissue hypoxia of the iodinated azomycin nucleoside class

Seven second-generation hypoxic markers of the iodinated azomycin nucleoside class have been synthesized and tested for hypoxia marking activity with tumor cells in vitro and in vivo. β-D-lodoazomycin galactoside (IAZG) and β-D-lodoazomycin xylopyranoside (IAZXP) demonstrated superior hypoxia marking properties relative to IAZA because of their higher water solubilities, rapid plasma clearance rates from tumor-bearing mice and maximum tumor/blood (T/B) and tumor/muscle (T/M) ratios. Our studies with animal tumor models show that T/B or T/M ratios of these markers determined by scintigraphy or planar imaging can predict for the relative degree of tumor hypoxia and for tumor radioresistance.