2',3',5'-Tri-O-acetylinosine Chemical Properties

Melting point:

234-236°C

Boiling point:

620.7±65.0 °C(Predicted)

Density 

1.62±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Methanol (Sparingly), Water (Sparingly)

form 

Solid

pka

2.96±0.20(Predicted)

color 

White

Stability:

Freezer

InChI

InChI=1S/C16H18N4O8/c1-7(21)25-4-10-12(26-8(2)22)13(27-9(3)23)16(28-10)20-6-19-11-14(20)17-5-18-15(11)24/h5-6,10,12-13,16H,4H2,1-3H3,(H,17,18,24)/t10-,12-,13-,16-/m1/s1

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)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

2',3',5'-Tri-O-acetylinosine Usage And Synthesis

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

An intermediate used for the synthesis of 6-substituted purine ribosides.

Uses

2',3',5'-Tri-O-acetylinosine is 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

2',3',5'-Tri-O-acetylinosine(3181-38-2)Related Product Information

• Inosine
• 2',3',5'-Triacetylinosine
• 2',3',5-TRI-O-ACETYL-8-BROMOGUANOSINE
• 2',3',5'-Triacetylguanosine
• 2',3',5'-TRI-O-ACETYLINOSINE
• Tri-O-acetyl-8-(allyloxy)guanosine
• guanosine 2',3',5'-tribenzoate
• 2',3',5'-TRI-O-ACETYL-2N,2N-DIMETHYL-GUANOSINE