15981-63-2

Basic information

• Product Name: 2',3',5'-TRI-O-ACETYLNEBULARINE
• Synonyms: 2',3',5'-TRI-O-ACETYLNEBULARINE;9-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)purine;9-β-D-Ribofuranosylpurine Triacetate;NSC 76765;9-beta-D-Ribofuranosylpurine triacetate;9-(2,3,5-Tri-O-acetyl-beta-D-ribofuranosyl)-9H-purine;9-(2,3,5-Tri-O-acetyl-beta-D-ribofuranosyl)purine
• CAS NO: 15981-63-2
• Molecular Formula: C₁₆H₁₈N₄O₇
• Molecular Weight: 378.34
• Product Categories: Bases & Related Reagents;Nucleotides
• Mol File: 15981-63-2.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 536.4°Cat760mmHg
• Flash Point: 278.2°C
• Appearance: /
• Density: 1.54g/cm³
• Vapor Pressure: 1.41E-11mmHg at 25°C
• Refractive Index: 1.65
• Solubility: Chloroform, Ethyl Acetate, Methanol
• PKA: 2.42±0.10(Predicted)
• CAS DataBase Reference: 2',3',5'-TRI-O-ACETYLNEBULARINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3',5'-TRI-O-ACETYLNEBULARINE(15981-63-2)
• EPA Substance Registry System: 2',3',5'-TRI-O-ACETYLNEBULARINE(15981-63-2)

Safety Data

• Hazardous Substances Data: 15981-63-2(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Oil

Uses

2’,3’,5’-Tri-O-acetylnebularine (cas# 15981-63-2) is a compound useful in organic synthesis.

InChI:InChI=1/C16H18N4O7/c1-8(21)24-5-12-13(25-9(2)22)14(26-10(3)23)16(27-12)20-7-19-11-4-17-6-18-15(11)20/h4,6-7,12-14,16H,5H2,1-3H3

Upstream product

• 3021-21-4 9-β-D-ribofuranosyl-6-thio-9H-purine 2',3',5'-triacetate 
• 1526929-31-6 C₁₆H₂₀N₆O₇ 
• 73237-86-2 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(methylthio)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 108-24-7 acetic anhydride 
• 550-33-4 Nebularin 
• 58-61-7 adenosine 
• 28708-32-9 1,2,3,5-tetra-O-acetyl-D-ribofuranose 
• 120-73-0 purine 
• 7387-57-7 triacetyladenosine 
• 74465-47-7 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-bromo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 290-87-9 1,3,5-Triazine 
• 53459-69-1 5-amino-1-(2,3,5-tris-O-acetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid 
• 120-73-0 purine 
• 13035-61-5 1,2,3,5-tetraacetylribose 

Downstream Products

• 1314804-25-5 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(m-tolyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 83026-93-1 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-phenyl-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 107037-26-3 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(2-phenyl-9H-purin-9-yl)tetrahydrofuran-3,4-diyldiacetate 
• 1512860-50-2 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-cyclohexyl-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 1512860-63-7 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(phenoxymethyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 14675-48-0 6-methyl-9-(β-D-ribofuranosyl)purine 
• 550-33-4 Nebularin 

Relevant articles and documents

Conversion of 9-substituted adenines to the corresponding purines: A simple deamination method for adenine derivatives

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Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO4 in water

A simple dehydrazination reaction has been achieved in the presence of a catalytic amount of CuSO4 for the first time. With CuSO4 (2 mol%) as a catalyst and water as a solvent, the dehydrazination products were obtained in good yields (66-95%). Moreover, the drugs nebularine and vidarabine were afforded successfully, and vidarabine could be produced on a 0.923 kg scale, which shows good potential for industrial applications.

Probing the reactivity of nebularine N1-oxide. A novel approach to C-6 C-substituted purine nucleosides

A novel approach to the synthesis of purine nucleoside analogues, featuring the reaction of the C6-N1-O- aldonitrone moiety of 9-ribosyl-purine (nebularine) N1-oxide with some representative dipolarophiles, as well as Grignard reagents, is repo

Microwave-assisted ribosylation of modified heterocyclic bases by Vorbrueggen method

During the last decades the nucleoside synthesis has proven to be important. The modified silyl-Hilbert-Johnson nucleoside synthesis modified by Vorbrueggen is one of the most often used methods. We have studied N-glycosilation of modifieded heterocyclic bases by Vorbrueggen method with microwave irradiation and we were able to shorten the reaction time and obtain higher yields. The method was demonstrated by fluoroquinolone and purine. Copyright Taylor & Francis Group, LLC.