3181-38-2

Basic information

• Product Name: 2',3',5'-TRIACETYLINOSINE
• Synonyms: INOSINE 2',3',5'-TRIACETATE;ACETICACID3,4-DIACETOXY-5-(6-HO-PURIN-9-YL)-TETR;2,3,5-TRIACETYLINOS;2',3',5'-Tri-O-acetyl-D-inosine;2,3,5-TRIACETYLINOSINE CRYSTALLINE;(2R,3S,4R,5R)-2-(ACETOXYMETHYL)-5-(6-OXO-1H-PURIN-9(6H)-YL)TETRAHYDROFURAN-3,4-DIYL DIACETATE;2'',3'',5''-TRI-O-ACETYL-INOSIN;2'-O,3'-O,5'-O-Triacetyl-6-hydroxy-6-deaminoadenosine
• CAS NO: 3181-38-2
• Molecular Formula: C₁₆H₁₈N₄O₈
• Molecular Weight: 394.34
• EINECS: 221-669-7
• Product Categories: Pharmaceutical Raw Materials;Bases & Related Reagents;Nucleotides
• Mol File: 3181-38-2.mol
• Article Data: 33

Chemical Properties

• Melting Point: 234-236°C
• Boiling Point: 620.7 °C at 760 mmHg
• Flash Point: 329.2 °C
• Appearance: White crystalline solid
• Density: 1.63 g/cm³
• Vapor Pressure: 1.12E-23mmHg at 25°C
• Refractive Index: 1.727
• Storage Temp.: −20°C
• Solubility: Methanol (Sparingly), Water (Sparingly)
• PKA: 2.96±0.20(Predicted)
• Stability: Freezer
• CAS DataBase Reference: 2',3',5'-TRIACETYLINOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3',5'-TRIACETYLINOSINE(3181-38-2)
• EPA Substance Registry System: 2',3',5'-TRIACETYLINOSINE(3181-38-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 3181-38-2(Hazardous Substances Data)

Usage

Description

2',3',5'-Tri-O-acetylinosine is a white crystalline solid that serves as an intermediate in the synthesis of 6-substituted purine ribosides. It has been demonstrated to inhibit the growth of cancer cells and is also an efficient method for bond cleavage and radiation protection. Additionally, it has the ability to bind to pyridinium ions and has been utilized in the synthesis of tetrapeptides with hydroxyl groups or alkylation.

Uses

Used in Pharmaceutical Industry:
2',3',5'-Tri-O-acetylinosine is used as an intermediate in the synthesis of 6-substituted purine ribosides for the development of pharmaceutical compounds.
Used in Cancer Research:
2',3',5'-Tri-O-acetylinosine is used as an inhibitor of cancer cell growth, providing a potential therapeutic approach for cancer treatment.
Used in Chemical Synthesis:
2',3',5'-Tri-O-acetylinosine is used as an efficient method for bond cleavage and radiation protection in various chemical synthesis processes.
Used in Peptide Synthesis:
2',3',5'-Tri-O-acetylinosine is used in the synthesis of tetrapeptides with hydroxyl groups or alkylation, contributing to the development of novel peptide-based compounds.

InChI:InChI=1/C16H18N4O8/c1-6(21)10(24)11-15(26,7(2)22)16(27,8(3)23)14(28-11)20-5-19-9-12(20)17-4-18-13(9)25/h4-5,10-11,14,24,26-27H,1-3H3,(H,17,18,25)/t10?,11-,14-,15-,16+/m1/s1

Upstream product

• 41623-91-0 2-bromo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)hypoxanthine 
• 5987-74-6 6-iodo-9-[β-(2',3',5'-tri-O-acetyl)-D-ribofuranosyl]purine 
• 863033-41-4 2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine 
• 108-24-7 acetic anhydride 
• 58-63-9 Inosine 
• 58-63-9 inosine 
• 7387-57-7 triacetyladenosine 
• 2466-76-4 N-Acetylimidazole 
• 1441063-52-0 2′,3′,5′-tri-O-acetyl-1-[(E)-2-(methoxycarbonyl)vinyl]inosine 
• 112-55-0 1-dodecylthiol 
• 123-56-8 Succinimide 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 127218-16-0 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{2-bromo-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-3-yl ester 
• 127211-14-7 2-Bromo-6-[2-(4-nitro-phenyl)-ethoxy]-9-trimethylsilanyl-9H-purine 

Downstream Products

• 659746-56-2 2',3',5'-tri-O-acetyl-1-[(benzyloxy)methyl]inosine 
• 51549-18-9 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(benzylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 190836-76-1 6-O-(4-chlorophenyl)inosine 
• 190836-74-9 2',3',5'-tri-O-acetyl-6-O-(4-chlorophenyl)inosine 
• 58-63-9 Inosine 
• 1394956-18-3 C₂₅H₃₅N₇O₄S 
• 15763-12-9 6-N-allyladenosine 
• 97374-48-6 N₆-cyclopentyladenosine 
• 17659-78-8 N₆-Isopentyladenosine 

Relevant articles and documents

Synthesis of isotopically labelled versions of adenosine agonist GR79236

Versions of adenosine receptor agonist GR79236, labelled either with carbon-14 at C-8 of the purine ring or with tritium in the cyclopentyl ring, were prepared in overall yields of 64% and 25% respectively. A mass labelled [M + 4] version containing carbon-13, nitrogen-15, and deuterium was also prepared in 3% yield.

SAICAR Synthesis method

A method of synthesizing SAICAR of the present invention is carried out at 5 - amino -1 - ((). 2R. 3R. 4S. 5R-3, 4 -dihydroxy -5 - (hydroxymethyl) tetrahydrofuran -2 -yl) -1H- Imidazol -4 - formamide is the starting material and is sequentially subjected to 5 - amino -1 - ((). 3aR. 4R. 6R. 6aR) -6 - (Hydroxymethyl) -2, 2 -dimethyltetrahydrofuran [3,4 -]d] [1, 3] Diox -4 - group) -1H-imidazole -4 -carboxamide. 5 - Amino -1 - (()3aR. 4R. 6R. 6aR) -6 - (Hydroxymethyl) -2, 2 -dimethyltetrahydrofuran [3,4 -]d] [1, 3] Diox -4 - group) -1H- Imidazole -4 - carboxylic acid, dibenzyl (5 - amino -1 -) (()3aR. 4R. 6R. 6aR) -6 - (Hydroxymethyl) -2, 2 -dimethyltetrahydrofuran [3,4 -]d] [1, 3] Diox -4 - group) -1H- Imidazol -4 - carbonyl) . LOf - aspartic acid and the like to obtain a finished product purity of up to 99.6%, impurities 0.4%, diastereomeric excess (de) values 97.3% and a yield 16.9%.

A process for preparing natural nucleoside powder clitocybin method

The invention discloses a new method for preparing natural nucleoside nebularine. According to the method disclosed by the invention, cheap inosine is used as a raw material and is subjected to three reactions including acyl protection, sulfuration and desulfuration to finally obtain the target product nebularine; in the desulfuration step, since 50% nitric acid is used as a desulfuration agent, such reaction conditions easily causing explosion as diazotization in the conventional synthesis method can be avoided, no heavy metal catalyst is used, no column chromatography is needed in the whole process, large-scale synthesis can be realized easily; and moreover, the new method for preparing natural nucleoside nebularine is suitable for research on medicine activity and further large-scale preparation.

Selective Acylation of Nucleosides, Nucleotides, and Glycerol-3-phosphocholine in Water

A convenient selective synthesis of 2′,3′-di-O-acetyl-nucleotide-5′-phosphates, 2′,3′-di-O-acetyl-nucleotide-5′-triphosphates and 2′,3′,5′-tri-O-acetyl-nucleosides in water has been developed. Furthermore, a long-chain selective glycerol-3-phosphocholine diacylation is elucidated. These reactions are environmentally benign, rapid, high yielding, and the products are readily purified. Importantly, this reaction may indicate a prebiotically plausible reaction pathway for the selective acylation of key metabolites to facilitate their incorporation into protometabolism.