4348-68-9

Usage

Uses

Used in Organic Synthesis:
2 3 5-TRI-O-BENZOYL-ALPHA-D-ARABINO-FURA is used as a key intermediate in the synthesis of various complex organic molecules. Its unique structure and reactivity allow for selective reactions and the formation of diverse chemical products.
Used in Pharmaceutical Industry:
2 3 5-TRI-O-BENZOYL-ALPHA-D-ARABINO-FURA is used as a building block for the development of novel pharmaceutical compounds. Its unique structure and reactivity can be exploited to design and synthesize new drugs with improved therapeutic properties.
Used in Medicinal Chemistry:
2 3 5-TRI-O-BENZOYL-ALPHA-D-ARABINO-FURA is used as a versatile tool in medicinal chemistry for the design and optimization of bioactive molecules. Its unique structure and reactivity can be utilized to explore new chemical space and identify potential drug candidates with novel mechanisms of action.

InChI:InChI=1/C26H21BrO7/c27-23-22(34-26(30)19-14-8-3-9-15-19)21(33-25(29)18-12-6-2-7-13-18)20(32-23)16-31-24(28)17-10-4-1-5-11-17/h1-15,20-23H,16H2/t20-,21-,22+,23+/m1/s1

Upstream product

• 7473-42-9 methyl tri-O-benzoyl-α-D-arabinofuranoside 
• 10323-20-3 D-Arabinose 
• 98-88-4 benzoyl chloride 
• 28697-53-2 D-arabinopyranose 
• 532-20-7 α-arabinofuranose 

Downstream Products

• 7473-42-9 methyl tri-O-benzoyl-α-D-arabinofuranoside 
• 97747-01-8 1,2,3,5-tetra-O-benzoyl-α-D-arabinofuranose 
• 7473-41-8 O¹,O³,O⁵-Tribenzoyl-β-D-arabinofuranose 
• 126990-53-2 Allyl O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 171074-30-9 (2S,3R,5R)-3-Azido-2-benzoyloxy-5-(2',3',5'-tri-O-benzoyl-α-D-arabinofuranosyloxy)cyclohexanone ethylene dithioacetal 
• 171074-29-6 (2S,3R,5R)-2,3-Dibenzoyloxy-5-(2',3',5'-tri-O-benzoyl-α-D-arabinofuranosyloxy)cyclohexanone ethylene dithioacetal 
• 171074-32-1 (2S,3R,5R)-3-Azido-2-benzoyloxy-5-(2',3',5'-tri-O-benzoyl-α-D-arabinofuranosyloxy)cyclohexanone O-benzyl oxime 
• 204124-81-2 octyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 
• 250693-31-3 1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2-acetamidoimidazole 
• 250693-33-5 1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2-trifluoroacetamidoimidazole 
• 316354-46-8 2,3,5-tri-O-benzoyl-β-D-arabinofuranosyl azide 
• 638188-77-9 8-azidooctyl 2,3,5-tri-O-benzoyl-α/β-D-arabinofuranoside 
• 765274-01-9 3,5-di-O-benzoyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate) 
• 103702-71-2 benzyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 

Relevant academic research and scientific papers

A practical silicon-free strategy for differentiation of hydroxy groups in arabinofuranose derivatives

Effective differentiation of 3,5-diol system and 2-hydroxy group in arabinofuranose derivatives, which is required for the preparation of building blocks useful for the synthesis of nucleoside analogues and oligosaccharide fragments of mycobacterial arabinogalactan and lipoarabinomannan, was achieved by using 3,5-di-O-benzoyl-1,2-O-benzylidene-βD-arabinofuranose or 3-O-(chloroacetyl)-β- d-arabinofuranose 1,2,5-orthobenzoate, both readily accessible from inexpensive methylα-d-arabinofuranoside via the corresponding glycosyl bromides. The use of expensive organosilicon protecting groups is completely avoided in this novel strategy, a feature that makes it amenable to scale-up. Georg Thieme Verlag Stuttgart New York.

Design, synthesis and activity of thio-linked arabinofuranosyl disaccharides against mycobacterial tuberculosis (MTB) and Mycobacterium avium complex (MAC)

We report the chemical synthesis of a series of disaccharides of arabinofuranose with a glycosidic sulfur linker as mimics of the acceptor for arabinofuranosyltransferases with and without using any activator to avoid any complex reactions. These analogs were tested for in vitro activity against MTB strain H37Ra and 3 MAC clinical isolates. MICs were determined using a colorimetric microdilution broth assay. Bactericidal activity was studied with kill curves over a period of seven days. Intracellular activity against MTB H37Ra was determined in the Mono Mac 6 (MM6) human monocytic cell line. ARKAT-USA, Inc.

Ring opening of acylated β-d-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks

β-d-Arabinofuranose 1,2,5-orthobenzoates with 3-O-acetyl, 3-O-benzoyl, and 3-O-chloroacetyl groups were prepared in an efficient manner starting from readily available crystalline methyl 2,3,5-tri-O-benzoyl-α-d- arabinofuranoside, and ring-opening reactio

Synthesis of iodoaminoimidazole arabinoside (IAIA): A potential reductive metabolite of the spect imaging agent, iodoazomycin arabinoside (IAZA)

The stereospecific synthesis of 1-(5-deoxy-5-iodo-α-D- arabinofuranosyl)-2-aminoimidazole (iodoaminoimidazole arabinoside: IAIA, 2) is described. The reaction of the protected sugar bromide (8) and trifluoroacetamidoimidazole (10B) gave the coupled produc

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.

Synthesis of new pseudodisaccharide aminoglycoside antibiotics from carbohydrates

Novel pseudodisaccharide-type aminocyclitol antibiotic models, built up from D-arabinose, D-ribose, D-glucosamine, L-ristosamine and L-acosamine have been synthesized by the glycosylation of suitably protected (azido)deoxyinosose aglycones derived by the Ferrier carbocyclic ring transformation of carbohydrate precursors. An alternative approach to related pseudodisaccharides, based on the Ferrier carbocyclization of reducing disaccharides, has also been elaborated. This latter method extends the scope of the Ferrier reaction, by demonstrating that acid-labile 2-deoxydisaccharides can also be readily transformed into the corresponding pseudodisaccharides under the slightly acidic conditions of this ring-transformation.