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

HRID 2361725
ノート
印刷プレビュー

反応式

HRID 2361725 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-882d5776bf6f476f956ae2a3d5e77893
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08691788B2

反応ノート

読み込み中…

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