3068-29-9

Usage

Uses

Used in Organic Synthesis:
TRI-O-ACETYL-BETA-D-ARABINOSYLBROMIDE is used as a reagent for the synthesis of complex sugar derivatives, particularly in organic chemistry. Its high reactivity and ability to selectively modify sugar molecules contribute to its importance in this field.
Used in Carbohydrate Chemistry Research:
In the field of carbohydrate chemistry, TRI-O-ACETYL-BETA-D-ARABINOSYLBROMIDE is used as a key tool for studying glycosidic linkages and the development of novel pharmaceuticals and agrochemicals. Its applications in this area highlight its significance in advancing carbohydrate-related research and development.
Used in Pharmaceutical Development:
TRI-O-ACETYL-BETA-D-ARABINOSYLBROMIDE is utilized as a component in the development of new pharmaceuticals, where its unique properties can be harnessed to create innovative drug candidates with potential therapeutic benefits.
Used in Agrochemical Development:
Similarly, in the agrochemical industry, TRI-O-ACETYL-BETA-D-ARABINOSYLBROMIDE is employed in the development of new agrochemical products, leveraging its reactivity and sugar modification capabilities to enhance crop protection and yield.

InChI:InChI=1/C11H15BrO7/c1-5(13)17-8-4-16-11(12)10(19-7(3)15)9(8)18-6(2)14/h8-11H,4H2,1-3H3/t8-,9-,10+,11-/m1/s1

Upstream product

• 506-96-7 Acetyl bromide 
• 10323-20-3 D-Arabinose 
• 108-24-7 acetic anhydride 
• 19186-37-9 1,2,3,4-tetra-O-acetyl-α-D-arabinopyranose 
• 28697-53-2 D-arabinopyranose 
• 25243-38-3 1,2,3,4-tetra-O-acetyl-β-D-arabinopyranose 
• 6748-95-4 β-D-arabinopyranose 
• 608-45-7 α-D-arabinopyranose 
• 1194778-66-9 2,3,4-tri-O-acetyl-D-arabinopyranose 
• 108646-05-5 (3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 

Downstream Products

• 52544-91-9 1-deoxy-1-C-(phenylthio)-2,3,4-tri-O-acetyl-D-arabinopyranose 
• 109015-94-3 tri-O-acetyl-S-carbamimidoyl-1-thio-α-D-arabinopyranose; hydrobromide 
• 151557-73-2 Benzyl 2,3,4-Tri-O-acetyl-α-D-arabinopyranoside 
• 91-09-8 (2S,3S,4R,5R)-2-Methoxy-tetrahydro-pyran-3,4,5-triol 
• 3152-43-0 3,4-di-O-acetyl-D-arabinal 
• 171973-25-4 Acetic acid (2R,3S,4R,5R)-4,5-diacetoxy-2-(pyrimidin-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester 
• 15054-61-2 2,2'-[methylenebis(thio)]bis(pyrimidine) 
• 19834-93-6 chloro(pyrimidin-2-ylthio)methane 
• 188783-51-9 Acetic acid (2R,3S,4R,5R)-4,5-diacetoxy-2-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-3-yl ester 
• 85620-92-4 2-((3S,4S)-4-Hydroxy-3,4-dihydro-2H-pyran-3-yl)-N-phenyl-acetamide 
• 85620-93-5 N,N-Dimethyl-2-((2S,5R)-5-phenylcarbamoylmethyl-5,6-dihydro-2H-pyran-2-yl)-acetamide 
• 85620-84-4 1,5-anhydro-2,3-dideoxy-D-glycero-pent-2-enitol 
• 87614-56-0 5S-iodo-1S,6S-3,7-dioxabicyclo<4,3,0>nonan-8-one 
• 85620-85-5 3R-3,6-dihydro-2H-pyranyl-N,N-dimethylacetamide 

Relevant academic research and scientific papers

Neuroprotective activity of different monosaccharide-modified gastrodin analogs

Gastrodin is a very important and well-known bioactive glycoside compound in Chinese medicine. It is also known as a drug with neuroprotective function. Here, a practical diversified synthesis of a series of gastrodin analogs was reported, which involved four-step procedures consisting of bromination, oxidation, etherification, and reduction. Various gastrodin analogs were obtained in good yields. The compound 4c in this study has a good neuroprotective function: it can significantly downregulate tumor necrosis factor-α and inducible nitric oxide synthase protein levels. The results of this study can provide a research basis for the development of neuroprotective drugs.

Synthesis of Functionalized 2-(4-Hydroxyphenyl)-3-methylbenzofuran Allosteric Modulators of Hsp90 Activity

Hsp90 is a molecular chaperone that plays a pivotal role in the cell life cycle. ATP-regulated internal dynamics are critical to Hsp90 function and we recently demonstrated that these dynamics can be modulated in an allosteric fashion; the protein C-terminal domain (CTD) can be effectively targeted with a family of 2-phenyl-benzofuran derivatives. Here we describe the expansion of the initial library, reporting 28 new derivatives that explore the chemical space at opposite ends of the benzofuran scaffold. Interactions of the compounds with a full-length protein homolog were explored by Saturation Transfer Difference (STD) NMR spectroscopy. In this context we also report the interaction epitope of Novobiocin, a known CTD inhibitor.

Synthesis of 9-O-glycosyl-berberine derivatives and bioavailability evaluation

To increase the bioavailability of berberine, three new 9-O-glycosyl-berberine derivatives, 9-O-glucosyl-(4a), 9-O-arabinosyl-(4b), and 9-O-erythrol-(4c) were obtained and confirmed by UV, 1HNMR, 13CNMR, and MS. The pharmacokinetic profiles of these synthetic compounds have been evaluated compared with berberine (1) and 9-O-alkyl-berberine (5) derivatives, which showed that maximum concentration (Cmax) and area under concentration-time curve (AUC) of 9-O-glycosyl-berberine increased dramatically. The results indicated that hydrophilic modification could significantly improve the bioavailability of berberine; 9-O-glycosyl-berberine might be a promising prodrug. Springer Science+Business Media, LLC 2011.

Novel olefin-phosphorus hybrid and diene ligands derived from carbohydrates

Starting from readily available monosaccharides d-glucose and d-arabinose, a family of novel chiral diene and olefin-phosphinite hybrid ligands has been designed. These ligands were prepared by attaching phosphinite or allylic donor sites onto unsaturated carbohydrate scaffolds. In rhodium(I)-catalysed conjugate addition of boronic acids to enones, the olefin-phosphinite hybrids gave products in up to 99% ee and above, whereas the dienes only led to modest enantioselectivity. However, by shifting the allylic donor sites from position 4 of the pyranose to the anomeric centre, an unexpected reversal of the stereoinduction process was observed. Georg Thieme Verlag Stuttgart New York.

Organometallic enantiomeric scaffolding: General access to 2-substituted oxa- and azabicyclo[3.2.1]octenes via a Bronsted acid catalyzed [5 + 2] cycloaddition reaction

6-Substituted TpMo(CO)2(η-2,3,4-pyranyl)- and TpMo(CO) 2(η-2,3,4-pyridinyl) scaffolds (Tp = hydridotrispyrazolylborato) function as reaction partners in an efficient regio- and stereocontrolled synthesis of functionalized oxa- and az

Tetraphenylbacteriochlorin derivatives and compositions containing the same

Provided is a tetraphenylbacteriochlorin derivative represented by the formula (I): 1[wherein R1, R2, R3 and R4, independently from each other, are a residue of a monosaccharide represented by the formulae: 2(wherein, R is a hydrogen or a protecting group)], or its salt. The tetraphenylbacteriochlorin derivative or its salt has a large molar extinction coefficient at long wavelengths which are expected to have a high tissue-penetrating property, and exhibits high selectivity to tumor cells and hydrophilicity.

Convenient chemoenzymatic synthesis of β-purine-diphosphate sugars (GDP-fucose-analogues)

A series of peracetylated β-sugar-1-phosphates with L-fuco configuration are efficiently prepared chemically and coupled in high yields to purine monophosphate bases via imidazolide activation. The resulting purine diphosphate sugars are deacetylated comp

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.

ENANTIOSPECIFIC SYNTHESES OF INTERMEDIATES IN THE TOTAL SYNTHESIS OF PSEUDOMONIC ACIDS

Enantiospecific syntheses of 1S,6S-3,7-dioxabicyclonon-4-en-8-one (1) and of the enantiomer (2) from D- and L-arabinose respectively have been achieved by two different routes.The conversion of (1) to 6S-(3R-acetanilido)-3,6-dihydro-2H-pyranyl-N,N-dimethylacetamide (3), a key intermediate in the synthesis of pseudomonic acids, is described.