| Identification | More | [Name]
2',3',5'-TRIACETYLINOSINE | [CAS]
3181-38-2 | [Synonyms]
2',3',5'-TRIACETYLINOSINE
2',3',5'-TRI-O-ACETYLINOSINE
ACETIC ACID (2R,3R,4R,5R)-4-ACETOXY-5-ACETOXYMETHYL-2-(6-OXO-1,6-DIHYDRO-PURIN-9-YL)-TETRAHYDRO-FURAN-3-YL ESTER
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
2'-O,3'-O,5'-O-Triacetylinosine
9-(2-O,3-O,5-O-Triacetyl-β-D-ribofuranosyl)-1H-purine-6(9H)-one
9-(2-O,3-O,5-O-Triacetyl-β-D-ribofuranosyl)-9H-purine-6-ol
Inosine triacetate | [EINECS(EC#)]
221-669-7 | [Molecular Formula]
C16H18N4O8 | [MDL Number]
MFCD00038617 | [Molecular Weight]
394.34 | [MOL File]
3181-38-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
234-236°C | [Boiling point ]
620.7±65.0 °C(Predicted) | [density ]
1.62±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Methanol (Sparingly), Water (Sparingly) | [form ]
Solid | [pka]
2.96±0.20(Predicted) | [color ]
White | [Usage]
An intermediate used for the synthesis of 6-substituted purine ribosides | [Stability:]
Freezer | [InChIKey]
SFEQTFDQPJQUJM-XNIJJKJLSA-N | [SMILES]
C(OC(=O)C)[C@H]1O[C@@H](N2C3C(=C(N=CN=3)O)N=C2)[C@H](OC(=O)C)[C@@H]1OC(=O)C | [CAS DataBase Reference]
3181-38-2(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
2',3',5'-Tri-O-acetylinosine has been shown to inhibit the growth of cancer cells, and is also an efficient method for bond cleavage and radiation protection. 2',3',5'-Tri-O-acetylinosine has been shown to bind to pyridinium ions, and it has been used in the synthesis of tetrapeptides with hydroxyl groups or alkylation. | [Chemical Properties]
White Crystalline Solid | [Uses]
2',3',5'-Tri-O-acetylinosine is an intermediate used for the synthesis of 6-substituted purine ribosides
| [Uses]
An intermediate used for the synthesis of 6-substituted purine ribosides. | [Synthesis]
To a suspension of inosine (10 g, 37.3 mmol) and a catalytic amount of 4-dimethylaminopyridine (DMAP) in acetonitrile (60 mL) were sequentially added triethylamine (20 mL, 143 mmol) and acetic anhydride (12.5 mL). The reaction mixture was stirred at room temperature for 1 hour, followed by the slow addition of methanol (5 mL). After continued stirring for 5 min, the reaction solution was concentrated under reduced pressure to give a white solid. The solid was washed with isopropanol to afford (2R,3R,4R,5R)-2-(acetyloxymethyl)-5-(6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyl diacetate (triacetoxyinosine, 12.1 g, 82% yield). | [References]
[1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 3, p. 462 - 470
[2] Synthesis, 2003, # 17, p. 2639 - 2642
[3] Journal of the American Chemical Society, 1997, vol. 119, # 32, p. 7423 - 7433
[4] Journal of Organic Chemistry, 1985, vol. 50, # 15, p. 2664 - 2667
[5] Chemistry - A European Journal, 2015, vol. 21, # 33, p. 11634 - 11643 |
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