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2,2-Dimethoxypropane → HCID 22854594、化合物

HRID 1647562
ノート
印刷プレビュー

反応式

HRID 1647562 の反応式
[C:1]([NH:16][C@@H:17]1[C@@H:46]([OH:47])[C@H:45]([OH:48])[C@@H:44]([CH2:49][OH:50])[O:43][C@@H:18]1[O:19][CH:20]([CH2:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[CH2:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C[O:52][C:53]([O:56]C)(C)C.[C:58]12([CH2:68]S(O)(=O)=O)C(C)(C)[CH:62]([CH2:63][CH2:64]1)[CH2:61][C:59]2=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH2:68]([O:56][C:53]([O:47][C@H:46]1[C@H:45]([OH:48])[C@@H:44]([CH2:49][OH:50])[O:43][C@H:18]([O:19][CH:20]([CH2:21][C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23])[CH2:32][C:33]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:34])[C@@H:17]1[NH:16][C:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:52])[C:58]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:59]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 64952,2-Dimethoxypropane2 回HCID 11430Potassium CarbonateHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-2 回HCID 15125697HCID 15125697、化合物

生成物 1

HCID 22854594HCID 22854594、化合物

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

In 15 ml of dried methylene chloride was dissolved 2.32 g of 2-benzyloxycarbonyl-1-(benzyloxycarbonylmethyl)ethyl 2-deoxy-2-tetradecanoylamino-α-D-glucopyranoside, and 2.04 ml of 2,2-dimethoxypropane and 38 mg of camphorsulfonic acid were added thereto at room temperature, followed by stirring at room temperature for 15 hours. Further, 20 mg of camphorsulfonic acid and 2.04 ml of 2,2-dimethoxypropane were added thereto, and the stirring was continued for an additional period of 8 hours. The reaction mixture was neutralized with anhydrous potassium carbonate while stirring, washed successively with water and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The resulting yellow oily substance was dissolved in 20 ml of dried methylene chloride, and 0.40 ml of pyridine, 0.61 g of N,N-dimethylaminopyridine, and 0.71 ml of benzyloxycarbonyl chloride were successively added thereto at room temperature, followed by stirring at room temperature for 12 hours. The reaction mixture was washed successively with 1N hydrochloric acid, water, and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The resulting yellow oily substance was dissolved in 50 ml of a 90% acetic acid aqueous solution, and the solution was stirred at 90° C. for 30 minutes. After cooling, the solvent was removed by distillation under reduced pressure. Toluene was added to the residue and then removed by distillation under reduced pressure. Toluene addition and removal were repeated, and the resulting residue was purified by silica gel column chromatography (developing solvent: 5% acetone-containing chloroform, changed en route to 2% methanol-containing chloroform) to obtain a pale yellow oily substance. Recrystallization from hexane followed by filtration gave 2.42 g of the titled compound as a white solid. This solid could be recrystallized from hexane.

後処理

  1. additionwere added
  2. customat room temperature
  3. waitthe stirring was continued for an additional period of 8 hours
  4. stirringwhile stirring
  5. washwashed successively with water
  6. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. dissolutionThe resulting yellow oily substance was dissolved in 20 ml of dried methylene chloride
  9. addition0.40 ml of pyridine, 0.61 g of N,N-dimethylaminopyridine, and 0.71 ml of benzyloxycarbonyl chloride were successively added
  10. customat room temperature
  11. stirringby stirring at room temperature for 12 hours
  12. washThe reaction mixture was washed successively with 1N hydrochloric acid, water
  13. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
  14. customThe solvent was removed by distillation under reduced pressure
  15. dissolutionThe resulting yellow oily substance was dissolved in 50 ml of a 90% acetic acid aqueous solution
  16. stirringthe solution was stirred at 90° C. for 30 minutes
  17. temperatureAfter cooling
  18. customthe solvent was removed by distillation under reduced pressure
  19. additionToluene was added to the residue
  20. customremoved by distillation under reduced pressure
  21. additionToluene addition and removal
  22. customthe resulting residue was purified by silica gel column chromatography (developing solvent: 5% acetone-containing chloroform, changed en route to 2% methanol-containing chloroform)
  23. customto obtain a pale yellow oily substance
  24. customRecrystallization from hexane
  25. filtrationfollowed by filtration

出典と根拠

ORDレコード
ord-16ac52d08d8e41ffba74647e2b44b4fc
出典データセット
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05432267

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート