2',3',5'-Triacetylguanosine Chemical Properties

Melting point:

226-231 °C(lit.)

Boiling point:

529.64°C (rough estimate)

Density 

1.2901 (rough estimate)

refractive index 

1.7500 (estimate)

storage temp. 

2-8°C

solubility 

DMSO (Slightly)

pka

9?+-.0.20(Predicted)

form 

Solid

color 

White

InChI

InChI=1S/C16H19N5O8/c1-6(22)26-4-9-11(27-7(2)23)12(28-8(3)24)15(29-9)21-5-18-10-13(21)19-16(17)20-14(10)25/h5,9,11-12,15H,4H2,1-3H3,(H3,17,19,20,25)/t9-,11-,12-,15-/m1/s1

InChIKey

ULXDFYDZZFYGIY-SDBHATRESA-N

SMILES

C(OC(=O)C)[C@H]1O[C@@H](N2C3=C(C(NC(=N3)N)=O)N=C2)[C@H](OC(=O)C)[C@@H]1OC(=O)C

CAS DataBase Reference

6979-94-8(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29349990

MSDS

• Language:English Provider:2',3',5'-Triacetylguanosine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2',3',5'-Triacetylguanosine Usage And Synthesis

Chemical Properties

White Solid

Uses

2’,3’,5’-Tri-O-acetyl Guanosine (cas# 6979-94-8) is a compound useful in organic synthesis.

Synthesis

2.2 mL of acetic anhydride (22 mmol) was added slowly and dropwise to a suspension of guanosine (2 g, 7.0 mmol) that had been pre-dried for 2 days under high vacuum with P4O10 containing triethylamine (7.7 mL, 55.2 mmol) and N,N-dimethylaminopyridine (92 mg, 0.75 mmol) in 27 mL of acetonitrile, and the reaction was carried out at 0°C. The mixture was stirred until homogeneous and the reaction was subsequently continued for 3 h at room temperature. After completion of the reaction, the reaction was quenched with methanol (2.3 mL). The reaction volume was concentrated to 1/3 of the original volume using a rotary evaporator, followed by the slow addition of ether to induce the precipitation of a fine white powder. The product was collected by filtration, washed with ether, and then stirred with acetone (30 mL) at 50 °C for 2 hours. A final 2.8 g (98% yield) of fine white powder product was obtained. The product was confirmed by 1H NMR (200 MHz, DMSO) and 13C NMR (200 MHz, CDCl3) analysis, and the mass spectrometry results were in accordance with the theoretical values (C18H21N5O5 [M+H]+ calculated value: 410.1306, measured value: 410.1305).

References

[1] Journal of the American Chemical Society, 2005, vol. 127, # 51, p. 18133 - 18142
[2] Synthesis, 1986, # 5, p. 385 - 386
[3] Nucleosides, Nucleotides and Nucleic Acids, 2007, vol. 26, # 6-7, p. 651 - 654
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 15, p. 4781 - 4789
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4660 - 4668

2',3',5'-Triacetylguanosine(6979-94-8)Related Product Information

• Guanosine
• Guanosine 5'-monophosphate disodium salt
• Acyclovir
• 5'-Guanylic acid
• 2',3',5'-Tri-O-acetyluridine
• L-Guanosine
• Guanine
• N-(1,3-Benzodithiol-2-yl)-2'-O,3'-O,5'-O-triacetylguanosine
• N-Methyl-N-[[(4-methylphenyl)thio]methyl]-2'-O,3'-O,5'-O-triacetylguanosine
• 2',3',5-TRI-O-ACETYL-8-BROMOGUANOSINE
• Tri-O-acetyl-8-(allyloxy)guanosine
• TIMTEC-BB SBB006223
• guanosine 2',3',5'-tribenzoate
• 2',3',5'-TRI-O-ACETYL-2N,2N-DIMETHYL-GUANOSINE
• 2',3',5'-Triacetylguanosine