Methanol → HCID 178504346、化合物

HRID 1167049ノート

反応式

HRID 1167049 の反応式
[C:1]([C@@:5]1([OH:29])[C@@H:9]([CH2:10][O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[O:8][C@@:7]([SiH:26]([CH3:28])[CH3:27])([N:16]2[C:25]3[N:24]=[CH:23][N:22]=[C:20]([NH2:21])[C:19]=3[N:18]=[CH:17]2)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C[OH:31]>CCO.O.C(Cl)Cl>[C:1]([C@@:5]1([OH:29])[C@@H:9]([CH2:10][O:11][C:12]([CH3:15])([CH3:13])[CH3:14])[O:8][C@@:7]([SiH:26]([CH3:27])[CH3:28])([N:16]2[C:25]3[N:24]=[CH:23][N:22]=[C:20]([NH2:21]=[O:31])[C:19]=3[N:18]=[CH:17]2)[CH2:6]1)([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 2

HCID 887MethanolHCID 178504348HCID 178504348、化合物

生成物 1

HCID 178504346HCID 178504346、化合物収率 39%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 3′,5′-O-bis-tert.-butyldimethylsilyl-2′-deoxyadenosine (Ogilvie, K. K. (1973) Can. J. Chem. 51, 3799-3807.) (6.0 g, 12.5 mmol) in a mixture of EtOH and H2O (2.5:1) was added at RT monopermaleic acid (24 mmol). After 2 days, another 6 equiv. of monopermaleic acid were added, and the reaction continued for two weeks. Continuous monitoring (TLC on SiO2, 10% MeOH in CH2Cl2) showed that the reaction did not proceed to completion even though peracid was still detectable (KI test). After two weeks, CH2Cl2 was added, the organic phase extracted with saturated NaHCO3, and 3′,5′-O-bis-tert.-butyldimethylsilyl-2′-deoxyadenosine N-oxide (3.41 g, 55%) isolated by chromatography (SiO2, EtOAc:hexane 4:1) together with starting material (2.33 g, 39%).

後処理

  1. waitthe reaction continued for two weeks
  2. waitAfter two weeks
  3. extractionthe organic phase extracted with saturated NaHCO3, and 3′,5′-O-bis-tert.-butyldimethylsilyl-2′-deoxyadenosine N-oxide (3.41 g, 55%)

出典と根拠

ORDレコード
ord-78d9dd5a428849b39d85778c2b5fef2c
出典データセット
uspto-grants-2003_09
特許番号
US06617106B1

反応ノート

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