Methanol → HCID 14859953, compound

HRID 260159Notes

Reaction equation

HRID 260159 reaction equation
[C:1]([O:20][CH2:21][C@H:22]1[O:26][C@@H:25]([N:27]2[C:36]3[N:35]=[CH:34][N:33]=[C:31]([NH2:32])[C:30]=3[N:29]=[CH:28]2)[C@H:24]([OH:37])[C@@H:23]1[OH:38])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](=O)CC[CH2:46][CH3:47])CCC.[S:49](Cl)([C:52]([F:55])([F:54])[F:53])(=[O:51])=[O:50].C[OH:58]>>[C:46]([O:38][C@@H:23]1[C@@H:22]([CH2:21][O:20][C:1]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:26][C@@H:25]([N:27]2[C:36]3[N:35]=[CH:34][N:33]=[C:31]([NH2:32])[C:30]=3[N:29]=[CH:28]2)[C@@H:24]1[O:37][S:49]([C:52]([F:55])([F:54])[F:53])(=[O:51])=[O:50])(=[O:58])[CH3:47]

Participants

5

Reactant 4

HCID 887MethanolHCID 61221Dibutyltin oxideHCID 79000Trifluoromethanesulfonyl chlorideHCID 8743118048-85-6

Product 1

HCID 14859953HCID 14859953, compound

Procedure

A mixture of 5'-O-trityladenosine (497 mg, 1 mmol) and dibutyltin oxide (249 mg, 1 mmol) in methanol (50 mL) is heated under reflux until a clear solution is obtained. The solution is concentrated in vacuo, the residue dissolved in dimethylformamide (20 mL). To the ice cooled solution is added triflyl chloride (190 mg, 1.1 mmol), and the mixture stirred for 90 minutes at room temperature, and then concentrated in vacuo. The residue is dissolved in pyridine (20 mL), and the solution treated with acetic anhydride (1.5 mL). After being stirred for 3 hours at room temperature, the mixture is concentrated in vacuo. The residue is chromatographed on a silica gel using a mixture of chloroform and ethanol (33:1 v/v) as the eluent to give 3'-O-acetyl-2'-O-triflyl-5'-O-trityladenosine (208 ) mg, 31% ) as a foam. 1H NMR (Me2SO-d6) δ 2.12 (3H, s, OAc), 3.36-3.49 (2H, m, H-5'5"), 4.36-4.40 (1H, m, H-4'), 5.90-5.95 (1h, m, H-3'), 6.45-6.54 (2H, m, H-1',2'), 7.20-7.57 (17H, m, Tr, NH2), 8.06, 8.35 (1H each, s, H-2, H-8). Analyses: Calculated for C32H28F3N5O7S: C, 71.94, H, 5.45, N, 10.24. Found: C, 71.67, H, 5.50, N, 10.27.

Workup

  1. temperatureis heated
  2. temperatureunder reflux until a clear solution
  3. customis obtained
  4. concentrationThe solution is concentrated in vacuo
  5. dissolutionthe residue dissolved in dimethylformamide (20 mL)
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue is dissolved in pyridine (20 mL)
  8. additionthe solution treated with acetic anhydride (1.5 mL)
  9. stirringAfter being stirred for 3 hours at room temperature
  10. concentrationthe mixture is concentrated in vacuo
  11. customThe residue is chromatographed on a silica gel using
  12. additiona mixture of chloroform and ethanol (33:1 v/v) as the eluent

Sources & evidence

ORD record
ord-bd5219ce5c0546aabe82eaefeb1c38f9
Source dataset
uspto-grants-1996_06
Patent number
US05525720

Reaction notes

Loading…