Potassium Carbonate → ((2S,5R)-5-(6-Amino-9H-purin-9-yl)-2,5-dihydrofuran-2-yl)methyl acetate

HRID 1030774

反応式

HRID 1030774 の反応式
C(O[C@@H:5]1[C@@H:9](Br)[C@@H:8]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[O:7][C@H:6]1[N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH2:25])(=O)C.[O-]S(S([O-])=O)=O.[Na+].[Na+].C([O-])([O-])=O.[K+].[K+].[Br-].[Br-].C([N+]1C=CC(C2C=C[N+](CCCCCCC)=CC=2)=CC=1)CCCCCC>C(Cl)Cl.O>[C:13]([O:12][CH2:11][C@H:8]1[O:7][C@@H:6]([N:16]2[C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH2:25])[C:22]=3[N:23]=[CH:24]2)[CH:5]=[CH:9]1)(=[O:15])[CH3:14]

参加物

7

反応物 4

HCID 11430Potassium Carbonate2 回HCID 24489Sodium DithioniteHCID 802621,1'-Diheptyl-4,4'-bipyridinium dibromide2 回HCID 109825609-(2,5-di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)adenine

生成物 1

HCID 11022122((2S,5R)-5-(6-Amino-9H-purin-9-yl)-2,5-dihydrofuran-2-yl)methyl acetate収率 83%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solvent mixture of 35 ml of methylene chloride and 15 ml of water were added 500 mg (1.21 mmol) of 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)adenine, 2.09 g (12.0 mmols) of Na2S2O4 and 995 mg (7.2 mmols) of K2CO3. The mixture was stirred for a while in an argon atmosphere. Then 308 mg (0.6 mmol) of N,N'-diheptyl-4,4'-bipyridinium dibromide was added and the mixture was stirred at 28° C. for 15 hours. Furthermore, 418 mg of Na2S2C4, 380 mg of K2CO3 and 185 mg (0.36 mmol) of N,N'-diheptyl-4,4'-bipyridinium dibromide were supplemented followed by stirring for 24 hours. To the mixture was added 50 ml of methylene chloride. The mixture was fractionated and the organic phase was dried over anhydrous magnesium sulfate. After filtering and concentration, the concentrate was purified by silica gel PTLC [Whatman PLK-5F, developed with ethyl acetate-methanol (8:1)] to give 276 mg (83%) of 5'-O-acetyl-2',3'-didehydro-2',3'-dideoxyadenosine.

後処理

  1. stirringthe mixture was stirred at 28° C. for 15 hours
  2. stirringby stirring for 24 hours
  3. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtering
  5. concentrationconcentration
  6. customthe concentrate was purified by silica gel PTLC [Whatman PLK-5F, developed with ethyl acetate-methanol (8:1)]

出典と根拠

ORDレコード
ord-fe7f1f89f20246688b3021a5b92e411c
出典データセット
uspto-grants-1992_04
特許番号
US05106962

関連ノート

読み込み中…