ChemicalBook--->CAS DataBase List--->6979-94-8

6979-94-8

6979-94-8 Structure

6979-94-8 Structure
IdentificationMore
[Name]

2',3',5'-Triacetylguanosine
[CAS]

6979-94-8
[Synonyms]

2',3',5'-TRIACETYLGUANOSINE
2',3',5'-TRI-O-ACETYLGUANOSINE
GUANOSINE 2',3',5'-TRIACETATE
TAG
TRIACETYLGUANOSINE
ACETIC ACID (2R,3R,4R,5R)-3,4-DIACETOXY-5-(2-AMINO-6-OXO-1,6-DIHYDRO-PURIN-9-YL)-TETRAHYDRO-FURAN-2-YLMETHYL ESTER
Guanosine Triacetate
NSC 66387
2',3',5'-Tri-O-acetyl-D-guanosine
2-(ACETOXYMETHYL)-5-(2-AMINO-6-OXO-1H-PURIN-9(6H)-YL)TETRAHYDROFURAN-3,4-DIYL DIACETATE
[(2R,3R,4R,5R)-4-Acetyloxy-5-(acetyloxymethyl)-2-(2-amino-6-oxo-3H-purin-9-yl)oxolan-3-yl] acetate
Tri-O-acetylguanosine
2',3',5'-O-Triacetylguanosine
2-Amino-9-(2-O,3-O,5-O-triacetyl-β-D-ribofuranosyl)-9H-purine-6-ol
[EINECS(EC#)]

230-242-4
[Molecular Formula]

C16H19N5O8
[MDL Number]

MFCD00057054
[Molecular Weight]

409.35
[MOL File]

6979-94-8.mol
Chemical PropertiesBack Directory
[Appearance]

White Solid
[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. ]

−20°C
[solubility ]

DMSO (Slightly)
[form ]

Solid
[pka]

9?+-.0.20(Predicted)
[color ]

White
[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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[Safety Statements ]

S24/25:Avoid contact with skin and eyes .
[WGK Germany ]

3
[HS Code ]

29349990
[Storage Class]

11 - Combustible Solids
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

2',3',5'-Triacetylguanosine(6979-94-8).msds
Hazard InformationBack Directory
[Chemical Properties]

White Solid
[Uses]

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

Acetic anhydride

108-24-7

Guanosine

118-00-3

2',3',5'-Triacetylguanosine

6979-94-8

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
Spectrum DetailBack Directory
[Spectrum Detail]

2',3',5'-Triacetylguanosine(6979-94-8)MS
2',3',5'-Triacetylguanosine(6979-94-8)1HNMR
2',3',5'-Triacetylguanosine(6979-94-8)13CNMR
2',3',5'-Triacetylguanosine(6979-94-8)IR1
2',3',5'-Triacetylguanosine(6979-94-8)IR2
2',3',5'-Triacetylguanosine(6979-94-8)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

2',3',5'-Triacetylguanosine, 95%(6979-94-8)
[Sigma Aldrich]

6979-94-8(sigmaaldrich)
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