Thymidine → 5'-O-(9-Phenylxanthen-9-yl)thymidine

HRID 1488554ノート

反応式

HRID 1488554 の反応式
Cl[C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[C@@H:22]1([N:30]2[CH:38]=[C:36]([CH3:37])[C:34](=[O:35])[NH:33][C:31]2=[O:32])[O:29][C@H:26]([CH2:27][OH:28])[C@@H:24]([OH:25])[CH2:23]1>N1C=CC=CC=1.C(Cl)Cl>[C:16]1([C:2]2([O:28][CH2:27][C@H:26]3[O:29][C@@H:22]([N:30]4[CH:38]=[C:36]([CH3:37])[C:34](=[O:35])[NH:33][C:31]4=[O:32])[CH2:23][C@@H:24]3[OH:25])[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=3[O:9][C:10]3[C:15]2=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

5

反応物 2

HCID 5789ThymidineHCID 1706559-Chloro-9-phenyl-9H-xanthene

生成物 1

HCID 109731175'-O-(9-Phenylxanthen-9-yl)thymidine収率 65%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

585 mg (2 mmol) of 9-chloro-9-phenylxanthene were added to a solution of 484 mg (2 mmol) of thymidine in 20 ml of pyridine, and the resulting mixture was stirred at room temperature for 1 hour whilst shading it from light. The reaction mixture was then diluted with 200 ml of methylene chloride, and the diluted mixture was washed twice, each time with 200 ml of a 5% w/v aqueous solution of sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through 35 g of silica gel (70-230 mesh), using methylene chloride containing from 0 to 2.5% by volume of methanol as the eluent, to give 647.8 mg (yield 65%) of the title compound. 1H Nuclear Magnetic Resonance Spectrum (CDCl3, 270 MHz, TMS), δ ppm:

後処理

  1. washthe diluted mixture was washed twice
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by distillation under reduced pressure
  4. customThe residue was purified by column chromatography through 35 g of silica gel (70-230 mesh)

出典と根拠

ORDレコード
ord-dc04f0f954cd4ca2be0dcd3708e53027
出典データセット
uspto-grants-1997_10
特許番号
US05674856

反応ノート

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