Tetrabutylammonium Fluoride → N-Benzoyl-3'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2'-deoxyadenosine

HRID 968370Notes

Reaction equation

HRID 968370 reaction equation
[C:1]([NH:9][C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:53]=2[N:54]=[CH:55][N:56]=1)[C@@H:15]1[O:52][C@H:42]([CH2:43][O:44][Si](C(C)(C)C)(C)C)[C@@H:17]([O:18][C:19]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([NH:9][C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:53]=2[N:54]=[CH:55][N:56]=1)[C@@H:15]1[O:52][C@H:42]([CH2:43][OH:44])[C@@H:17]([O:18][C:19]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:16]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 23397587HCID 23397587, compound

Product 1

HCID 15928822N-Benzoyl-3'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2'-deoxyadenosineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

N6-benzoyl-5′-O-(tert-butyldimethylsilyl)-3′-O-(4,4′-dimethoxytrityl)-2′-deoxyadenosine (16.2 g) was dissolved in 200 ml of dry THF. A THF solution (31 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, THF was distilled off and extraction using chloroform was carried out. The extract was then 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 13.8 g of the titled compound as a white powder (yield: 98%).

Workup

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

Sources & evidence

ORD record
ord-ad5f0a8edef340b99308d2d238d3dafc
Source dataset
uspto-grants-2005_10
Patent number
US06958391B2

Reaction notes

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