Tetrabutylammonium Fluoride → 2'-Deoxy-3'-O-DMT-N2-Isobutyrylguanosine

HRID 968367Notes

Reaction equation

HRID 968367 reaction equation
[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:54])[C:10]2[N:11]=[CH:12][N:13]([C:52]=2[N:53]=1)[C@@H:14]1[O:51][C@H:41]([CH2:42][O:43][Si](C(C)(C)C)(C)C)[C@@H:16]([O:17][C:18]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:15]1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:54])[C:10]2[N:11]=[CH:12][N:13]([C:52]=2[N:53]=1)[C@@H:14]1[O:51][C@H:41]([CH2:42][OH:43])[C@@H:16]([O:17][C:18]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:15]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 136334533N2-isobutyryl-5'-O-(tert-butyldimethylsilyl)-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosin

Product 1

HCID 1363345442'-Deoxy-3'-O-DMT-N2-IsobutyrylguanosineYield 60.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

N2-isobutyryl-5′-O-(tert-butyldimethylsilyl)-3′-O-(4,4′-dimethoxytrityl)-2′-deoxyguanosine (25 g) was dissolved in 200 ml of dry THF. A THF solution (40 ml) of tetrabutylammonium fluoride was added to the resultant solution and 100 ml of dry THF was further added, followed by stirring at room temperature. After 8 hours, extraction using chloroform was carried out, and the extract was washed by a saturated solution of sodium chloride and dried with anhydrous magnesium sulfate. The extract was then concentrated and purified by column chromatography (ethyl acetate/hexane/methanol) to obtain 12.9 g of the titled compound as a white powder (yield: 60%).

Workup

  1. additionwas further added
  2. extractionextraction
  3. washthe extract was washed by a saturated solution of sodium chloride
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationThe extract was then concentrated
  6. custompurified by column chromatography (ethyl acetate/hexane/methanol)

Sources & evidence

ORD record
ord-907ca6a33dea42c7a8f283fdbc33fdae
Source dataset
uspto-grants-2005_10
Patent number
US06958391B2

Reaction notes

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