Tetrabutylammonium Fluoride → HCID 22942417, compound

HRID 362691Notes

Reaction equation

HRID 362691 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C@H:12]([S:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:11]1[O:32][C:33]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([C:42]1[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=1)[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:24]([S:23][C@@H:12]1[C@H:11]([O:32][C:33]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[C:42]2[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=2)[C@@H:10]([CH2:9][OH:8])[O:14][C@H:13]1[N:15]1[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]1=[O:17])(=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22942424HCID 22942424, compound

Product 1

HCID 22942417HCID 22942417, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5'-O-(tert-Butyldimethylsilyl)-3'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-(benzoylthio)-uridine (1.4 mmole) was treated with 20 ml of 1.0M tetrabutylammonium fluoride in THF at room temperature for 16 hr. The solvent was removed and the residue was purified on silica gel column chromatography to provide 2'-(benzoylthio)-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-7b1db307d9a44dbbab61e94385a4db22
Source dataset
uspto-grants-1999_02
Patent number
US05869696

Reaction notes

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