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Dimethyl Sulfoxide → Acetic Acid 4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-formyl-tetrahydro-furan-3-yl Ester

HRID 642932
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HRID 642932 반응식
ClC(Cl)(Cl)C(OC(=O)C(Cl)(Cl)Cl)=O.CS(C)=O.[C:18]([Si:22]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[O:23][CH:24]1[CH:28]([CH2:29][OH:30])[O:27][CH:26]([N:31]2[CH:36]=[CH:35][C:34](=[O:37])[NH:33][C:32]2=[O:38])[CH:25]1[O:39][C:40](=[O:42])[CH3:41])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:18]([Si:22]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[O:23][CH:24]1[CH:28]([CH:29]=[O:30])[O:27][CH:26]([N:31]2[CH:36]=[CH:35][C:34](=[O:37])[NH:33][C:32]2=[O:38])[CH:25]1[O:39][C:40](=[O:42])[CH3:41])([CH3:19])([CH3:20])[CH3:21]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 20079Trichloroacetic anhydrideHCID 66774584Acetic Acid 4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-tetrahydro-furan-3-yl Ester

생성물 1

HCID 86594161Acetic Acid 4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-formyl-tetrahydro-furan-3-yl Ester

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of trichloroacetic anhydride (1.5 eq.) and dimethylsulfoxide (2.0 eq.) in dichloromethane at −78° C. is added a solution of Compound 9 in dichloromethane. After 30 minutes, triethylamine (4.5 eq.) is added. Subsequently, the mixture is poured into ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, and evaporated to dryness. The resulting material is carried into the next step without further purification. This procedure has been used to prepare the related 4′-C-α-formyl nucleosides (Nomura, M., et. al., J. Med. Chem. 1999, 42, 2901-2908).

후처리

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe resulting material is carried into the next step without further purification
  5. customto prepare the related 4′-C-α-formyl nucleosides (Nomura, M., et. al., J. Med. Chem. 1999, 42, 2901-2908)

출처 및 근거

ORD 기록
ord-0df10ea6235445dca721d1d37702fc35
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07696345B2

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