5987-73-5

Basic information

• Product Name: 2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9-?-D-RIBOFURANOSIDE
• Synonyms: 2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9-?-D-RIBOFURANOSIDE;9-(2',3',5'-Tri-O-acetyl-b-D-ribofuranosyl)-6-chloropurine;2',3',5'-Tri-O-acetyl-6-chloronebularine;6-Chloro-9-(2,3,5-tri-O-acetyl-β-D- ribofuranosyl)purine;6-Chloro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine;6-Chloro-9-β-D-ribofuranosyl-9H-purine 2',3',5'-Triacetate;NSC 281799;9-(2',3',5'-Tri-O-acetyl-beta-D-ribofuranosyl)-6-chloropurine
• CAS NO: 5987-73-5
• Molecular Formula: C₁₆H₁₇ClN₄O₇
• Molecular Weight: 412.78178
• Product Categories: Bases & Related Reagents;Nucleotides;Carbohydrates & Derivatives
• Mol File: 5987-73-5.mol
• Article Data: 45

Chemical Properties

• Melting Point: 161-162°C
• Boiling Point: 560.9°C at 760 mmHg
• Flash Point: 293°C
• Appearance: /
• Density: 1.62g/cm³
• Vapor Pressure: 1.31E-12mmHg at 25°C
• Refractive Index: 1.661
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform, Methanol (Sparingly)
• PKA: 0.76±0.10(Predicted)
• CAS DataBase Reference: 2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9-?-D-RIBOFURANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9-?-D-RIBOFURANOSIDE(5987-73-5)
• EPA Substance Registry System: 2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9-?-D-RIBOFURANOSIDE(5987-73-5)

Safety Data

• Hazardous Substances Data: 5987-73-5(Hazardous Substances Data)

Usage

Uses

2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside is a nucleoside compound with inhibitory activity on a rho-GTPase cell protein.

InChI:InChI=1/C16H17ClN4O7/c1-7(22)25-4-10-12(26-8(2)23)13(27-9(3)24)16(28-10)21-6-20-11-14(17)18-5-19-15(11)21/h5-6,10,12-13,16H,4H2,1-3H3

Upstream product

• 32865-86-4 6-chloro-9-trimethylsilylpurine 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 3181-38-2 2’,3’,5’-tri-O-acetylinosine 
• 16321-99-6 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 87-42-3 6-chloropurine 
• 63248-71-5 2',3',5'-tri-O-acetyl-β-arahypoxanthine 
• 7013-16-3 9-(β-D-arabinofuranosyl)-9H-purin-6(1H)-one 
• 28069-16-1 Acetic acid (2R,3R,4S,5R)-4-acetoxy-5-acetoxymethyl-2-(6-hydroxy-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 10517-16-5 9β-D-arabinofuranosylhypoxanthyne 
• 15830-52-1 (2R,3R,4S,5R)-2-(acetoxymethyl)-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 63248-71-5 C₁₆H₁₈N₄O₈ 
• 5536-17-4 arabinosyl adenine 
• 58-63-9 inosine 
• 108-24-7 acetic anhydride 

Downstream Products

• 31199-61-8 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(dimethylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 
• 15981-63-2 2',3',5'-tri-O-acetylnebularine 
• 2004-06-0 6-Chloropurine riboside 
• 132089-80-6 6-(4-chlorophenylsulfanyl)-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine 
• 1867-73-8 N⁶-methyladenosine 
• 773072-10-9 N⁶-(benzyloxycarbonylaminobutyl)adenosine 
• 84765-98-0 6-phenyl-9-(β-D-ribofuranosyl)-9H-purine 
• 3021-21-4 6-thio-9-(2',3',5'-tri-O-acetyl-β-D-ribosyl)purine 
• 16006-62-5 6-ethyl-9-β-D-ribofuranosylpurine 
• 69359-27-9 6-n-propyl-9-β-D-ribofuranosylpurine 
• 83026-93-1 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-phenyl-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 145047-44-5 6-methyl-9-(β-D-arabinofuranosyl)purine 
• 4229-50-9 N₆-methyl AMP 

Relevant articles and documents

Modification of Nucleic Acid Bases via Radical Intermediates: Synthesis of Dihalogenated Purine Nucleosides

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Phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled DNA and RNA

TEMPO spin labels protected with 2-nitrobenzyloxymethyl groups were attached to the amino residues of three different nucleo-sides: deoxycytidine, deoxyadenosine, and adenosine. The corresponding phosphoramidites could be incorporated by unmodified standa

Highly efficient chemical phosphorylation of 6-(4-phenylpiperazine-1-yl)-9-(β-D-ribofuranosyl)-9H-purine

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Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung

The one-step synthesis of the bench-stable hypervalent iodine reagents IndoleBX and PyrroleBX using mild Lewis acid catalyzed conditions is reported. The new reagents are stable up to 150 °C and were applied in the C?H arylation of unactivated arenes using either rhodium or ruthenium catalysts. A broad range of heterocyclic systems of high interest for synthetic and medicinal chemistry was accessed in high yields. The developed C?H functionalization could not be achieved using reported reagents or methods, highlighting the unique reactivity of Indole- and Pyrrole-BX.