3068-29-9

Basic information

• Product Name: TRI-O-ACETYL-BETA-D-ARABINOSYLBROMIDE
• Synonyms: β-D-Arabinopyranosylbromide,triacetate;tri-o-acetyl-β-d-arabinosylbromide;2-O,3-O,4-O-Triacetyl-β-D-arabinopyranosyl bromide;2,3,4-Tri-O-acetyl-beta-D-arabinopyranosyl bromide;beta-D-Arabinopyranosyl bromide triacetate;2,3,4-Tri-O-acetyl-beta-D-arabinopyranosyl broMide beta-D-Arabinopyranosyl broMide triacetate
• CAS NO: 3068-29-9
• Molecular Formula: C₁₁H₁₅BrO₇
• Molecular Weight: 339.14
• Mol File: 3068-29-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 136-140 °C(lit.)
• Boiling Point: 337.191°C at 760 mmHg
• Flash Point: 157.728°C
• Appearance: /
• Density: 1.517g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.501
• CAS DataBase Reference: TRI-O-ACETYL-BETA-D-ARABINOSYLBROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRI-O-ACETYL-BETA-D-ARABINOSYLBROMIDE(3068-29-9)
• EPA Substance Registry System: TRI-O-ACETYL-BETA-D-ARABINOSYLBROMIDE(3068-29-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 3068-29-9(Hazardous Substances Data)

Usage

General Description

TRI-O-ACETYL-BETA-D-ARABINOSYLBROMIDE is a chemical compound composed of three acetyl groups attached to a beta-D-arabinose sugar molecule, which in turn is linked to a bromine atom. It is commonly used as a reagent in organic synthesis, particularly in the synthesis of complex sugar derivatives. Its high reactivity and ability to selectively modify sugar molecules make it an important tool in carbohydrate chemistry. TRI-O-ACETYL-BETA-D-ARABINOSYLBROMIDE is also used in the study of glycosidic linkages and in the development of novel pharmaceuticals and agrochemicals. Overall, TRI-O-ACETYL-BETA-D-ARABINOSYLBROMIDE has important applications in organic chemistry and biochemistry, particularly in the field of carbohydrate research.

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

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

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 
• 1056028-73-9 (2R,3R,4R,5R)-acetic acid 3,5-diacetoxy-2-phenyltetrahydropyran-4-yl ester 
• 403822-05-9 4-(2',3',4'-tri-O-acetyl-β-D-arabinopyranosyloxy)benzaldehyde 
• 6638-76-2 methyl tri-O-benzoyl-α-D-arabinopyranoside 
• 4145-05-5 tri-O-benzoyl-1,5-anhydro-D-arabitol 
• 61134-26-7 benzyl α-D-arabinopyranoside 
• 130272-39-8 guanosine-5'-(α-D-arabinopyranosyl)-diphosphate 
• 85620-85-5 3R-3,6-dihydro-2H-pyranyl-N,N-dimethylacetamide 
• 87614-56-0 5S-iodo-1S,6S-3,7-dioxabicyclo<4,3,0>nonan-8-one 
• 85620-84-4 1,5-anhydro-2,3-dideoxy-D-glycero-pent-2-enitol 

Relevant articles and documents

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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.

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.