Methanol → HCID 178504346, 화합물

HRID 1167049노트

반응식

HRID 1167049 반응식
[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]

참가 물질

6

반응물 2

HCID 887MethanolHCID 178504348HCID 178504348, 화합물

생성물 1

HCID 178504346HCID 178504346, 화합물수율 39%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-78d9dd5a428849b39d85778c2b5fef2c
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06617106B1

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