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 1629689

反応式

HRID 1629689 の反応式
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]

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3382ea17cb554511900b75197dfbca89
出典データセット
uspto-grants-2014_07
特許番号
US08791083B2

関連ノート

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