Thymidine → 5'-O-(4,4'-Dimethoxytrityl)thymidine

HRID 2117803Notes

Reaction equation

HRID 2117803 reaction equation
[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[CH3:18][O:19][C:20]1[CH:41]=[CH:40][C:23]([C:24](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:22][CH:21]=1>N1C=CC=CC=1>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]([O:7][CH2:6][C@H:5]2[O:8][C@@H:1]([N:9]3[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]3=[O:11])[CH2:2][C@@H:3]2[OH:4])([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:23]2[CH:40]=[CH:41][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 5789ThymidineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)

Product 1

HCID 1624195'-O-(4,4'-Dimethoxytrityl)thymidine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Thymidine (1.918 g, 8.0 mmol) was dried under reduced pressure for a while, pyridine was then added in an argon atmosphere, and the mixture was stirred. 4,4′-Dimethoxytrityl chloride (DMTr-Cl) was added at 0° C., and the mixture was allowed to return to room temperature over about 2 hours with stirring. After confirmation of completion of the reaction by TLC, the reaction was quenched with water. This solution was concentrated under reduced pressure, the concentrate was dissolved in dichloromethane, and the solution was washed with a saturated aqueous solution of copper sulfate and with brine. The organic layer was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (MeOH:CH2Cl2=1:9). The eluate fraction was evaporated under reduced pressure, and the residue was dissolved in a small amount of ethyl acetate. Hexane was added to this solution for reprecipitation to give the title compound 5′-DMTr-Thd. Yield 3.67 g, 82.7%.

Workup

  1. additionwas then added in an argon atmosphere
  2. stirringwith stirring
  3. customAfter confirmation of completion of the reaction by TLC
  4. customthe reaction was quenched with water
  5. concentrationThis solution was concentrated under reduced pressure
  6. dissolutionthe concentrate was dissolved in dichloromethane
  7. washthe solution was washed with a saturated aqueous solution of copper sulfate and with brine
  8. customThe organic layer was evaporated under reduced pressure
  9. customthe residue was purified by silica gel chromatography (MeOH:CH2Cl2=1:9)
  10. customThe eluate fraction was evaporated under reduced pressure
  11. dissolutionthe residue was dissolved in a small amount of ethyl acetate
  12. additionHexane was added to this solution for reprecipitation

Sources & evidence

ORD record
ord-a9c3d24a016e42a2bf44abe9f4a29810
Source dataset
uspto-grants-2008_10
Patent number
US07442788B2

Reaction notes

Loading…