Hydrogen Peroxide → 8-trifluoromethyl-2',3',5'-tri-O-acetylguanosine

HRID 1363455Notes

Reaction equation

[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[C:29]2[N:28]=[C:26]([NH2:27])[NH:25][C:23](=[O:24])[C:22]=2[N:21]=[CH:20]1)(=[O:3])[CH3:2].S(=O)(=O)(O)O.[F:35][C:36](I)([F:38])[F:37].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[F:35][C:36]([F:38])([F:37])[C:20]1[N:19]([C:29]2[N:28]=[C:26]([NH2:27])[NH:25][C:23](=[O:24])[C:22]=2[N:21]=1)[C@@H:6]1[O:7][C@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:5]1[O:4][C:1](=[O:3])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

0.41 g (1.0 mmol) of 2′,3′,5′-tri-O-acetylguanosine was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 2.0 ml of dimethyl sulfoxide, 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 3.0 mol/l of dimethyl sulfoxide solution of trifluoromethyl iodide, 0.3 ml of a 1.0 mol/l aqueous solution of iron (II) sulfate and 0.2 ml of a 30% hydrogen peroxide aqueous solution. The mixture was stirred at 40 to 50° C. for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 8-trifluoromethyl-2′,3′,5′-tri-O-acetylguanosine (19F-NMR yield: 51%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 8-Trifluoromethyl-2′,3′,5′-tri-O-acetylguanosine was obtained as a yellow solid (0.22 g, yield: 47%) by silica gel column chromatography.

Workup

customplaced in a 50 ml two-neck flask
customequipped with a magnetic rotor
additionThe following materials were added
temperaturethe resulting solution was cooled to room temperature

Sources & evidence

ORD record: ord-3da9799b68ec49d4917387478c00c1e7
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884202B2

Reaction notes

Loading…