Tetrabutylammonium Fluoride → (2R,3R,4S,5R)-2-{2-[(Benzyloxy)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268370노트

반응식

HRID 2268370 반응식
[CH2:1]([O:8][CH2:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[C@H:19]2[C@H:23]([O:24][Si](C(C)(C)C)(C)C)[C@H:22]([O:32][Si](C(C)(C)C)(C)C)[C@@H:21]([CH2:40][O:41][CH3:42])[O:20]2)=[C:12]([NH:43][CH2:44][CH:45]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:8][CH2:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[C@H:19]2[C@H:23]([OH:24])[C@H:22]([OH:32])[C@@H:21]([CH2:40][O:41][CH3:42])[O:20]2)=[C:12]([NH:43][CH2:44][CH:45]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[N:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 695340912-[(Benzyloxy)methyl]-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-N-(2,2-diphenylethyl)-9H-purin-6-amine

생성물 1

HCID 9851252(2R,3R,4S,5R)-2-{2-[(Benzyloxy)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol수율 53.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

2-[(Benzyloxy)methyl]-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-N-(2,2-diphenylethyl)-9H-purin-6-amine (65 mg, 0.08 mmol) (preparation 24) was dissolved in stirred tetrahydrofuran (10 ml) and a 1 molar solution of tetra-n-butylammonium fluoride in tetrahydrofuran (0.5 ml, 0.5 mmol) added. The reaction mixture was stirred at room temperature for 15 min. The solvent was removed under reduced pressure and the residue partitioned between saturated aqueous sodium hydrogen carbonate solution and ethyl acetate. The ethyl acetate layer was separated, washed with brine and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a residue which was purified by column chromatography on silica gel eluting with a solvent system of ethyl acetate:hexane (3:1) increasing in polarity to ethyl acetate:methanol (97:3). This gave the title compound (25 mg) as a gum. MS: 604 (MNa+).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto give a residue which
  8. customwas purified by column chromatography on silica gel eluting with a solvent system of ethyl acetate:hexane (3:1)
  9. temperatureincreasing in polarity to ethyl acetate:methanol (97:3)

출처 및 근거

ORD 기록
ord-75731e54210441958a8c4ed79319fe64
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326359B1

반응 노트

불러오는 중…