Tetrabutylammonium Fluoride → 3'-[(Acetyloxy)methyl]-3'-deoxythymidine

HRID 2288279노트

반응식

HRID 2288279 반응식
[Si]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:22][C@@H:21]1[CH2:34][O:35][C:36](=[O:38])[CH3:37])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[C:36]([O:35][CH2:34][C@@H:21]1[C@@H:20]([CH2:19][OH:18])[O:24][C@@H:23]([N:25]2[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:22]1)(=[O:38])[CH3:37]

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 21969455HCID 21969455, 화합물

생성물 1

HCID 219694523'-[(Acetyloxy)methyl]-3'-deoxythymidine수율 57%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Compound 183 (2.00 g, 3.73 mmol) was dissolved in dry THF (36 ml) and tetrabutylammonium fluoride (8.8 ml, 1.0 M solution in THF, 2.4 equiv.) was added via syringe at room temperature under an atmosphere of argon. After completion of the reaction (1.5 hours), as was monitored by tlc in EtOAc (Rf 0.42), the solvent was removed in vacuo. The residue was purified by silica gel flash column chromatography in EtOAc/Hexane (4:6-9:1, v/v) to afford 184 (0.63 g, 57%) 1H NMR (CDCl3): δ8.89 (br, 1 H, NH), 7.55 (d, 1 H, J=1.1 Hz, H6), 6.13 (dd, 1 H, J=4.9, 6.6 Hz, H-1'), 4.17 & 4.09 (m, 2 H, CH2 -OAc), 4.07 (d, 1 H, J=11.7 Hz, H-5' & H-5'), 3.94-3.90 (m, 1 H, H-4'), 3.76 (d, 1H, J=11.7 Hz, H-5), 2.80-2.76 (m, 1 H, H-3'), 2.60 (br, 1 H, OH), 2.29-2.25 (m, 2 H, H2' & H-2"), 2.09 (s, 3 H, COCH3), 1.91 (s, 9 H, C(CH3)3); 13C NMR (CDCl3): 170.8 (C=O), 163.8 (C4), 150.3 (C2), 136.3 (C6), 110.8 (C5), 85.4 (C1'), 83.5 (C4'), 64.2 (C5'), 36.8 (C3'), 35 35.6 (C2'), 20.8, 12.5;

후처리

  1. customAfter completion of the reaction (1.5 hours)
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by silica gel flash column chromatography in EtOAc/Hexane (4:6-9:1

출처 및 근거

ORD 기록
ord-5fa0a808d94748b3bf096bcd1495aa89
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06087482

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