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Chlorotrimethylsilane → N2-Methoxytrityl-9-[(2R)-2-deoxy-2-C-ethynyl-2-fluoro-beta-D-erythro-pentofuranosyl]guanine

HRID 600668
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HRID 600668 반응식
[C:1]([C@@:3]1([F:21])[C@H:7]([OH:8])[C@@H:6]([CH2:9][OH:10])[O:5][C@H:4]1[N:11]1[CH:19]=[N:18][C:17]2[C:12]1=[N:13][CH:14]=[N:15][C:16]=2N)#[CH:2].C[Si](Cl)(C)C.CO[C:29]1[CH:48]=[CH:47][CH:46]=[CH:45][C:30]=1[C:31](Cl)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[NH4+:49].[OH-:50].C([O:54][CH2:55]C)(=O)C>N1C=CC=CC=1>[CH3:55][O:54][N:49]([C:31]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:30]1[CH:29]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:14]1[NH:15][C:16](=[O:50])[C:17]2[N:18]=[CH:19][N:11]([C@@H:4]3[O:5][C@H:6]([CH2:9][OH:10])[C@@H:7]([OH:8])[C@@:3]3([C:1]#[CH:2])[F:21])[C:12]=2[N:13]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 6397ChlorotrimethylsilaneHCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 14429619Methoxytrityl chlorideHCID 866247809-[(2R)2-Deoxy-2-C-ethynyl-2-fluoro-beta-D-erythro-pentofuranosyl]adenine

생성물 1

HCID 136343925
N2-Methoxytrityl-9-[(2R)-2-deoxy-2-C-ethynyl-2-fluoro-beta-D-erythro-pentofuranosyl]guanine

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a stirred solution of 7i (5.18 mmol) in pyridine (7 ml/mmol) was added trimethylsilyl chloride at room temperature. The mixture was stirred at room temperature for 6 hours. Methoxytrityl chloride (6.21 mmol) was then added and the reaction mixture was stirred at room temperature for 16 hours and 2 hours with NH4OH (4 ml/mmol). The mixture was diluted with ethyl acetate, washed with H2O, sat NaHCO3 solution and sat NaCl solution, dried over Na2SO4, filtered and evaporated. The crude material was purified by silica gel chromatography (DCM/MeOH) to yield the title compound. Yellowish oil. Molecular Formula C32H28FN5O5.

후처리

  1. washwashed with H2O
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified by silica gel chromatography (DCM/MeOH)

출처 및 근거

ORD 기록
ord-3e53c570e06d40b499ad3de21102a3c2
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07902202B2

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