Acetone → Diacetone-D-glucose

HRID 358128

반응식

HRID 358128 반응식
[CH3:1][C:2]([CH3:4])=[O:3].O=[CH:6][C@@H:7]([C@H:9]([C@@H:11]([C@@H:13]([CH2:15][OH:16])[OH:14])[OH:12])[OH:10])[OH:8].I.N1C=C[CH:21]=[CH:20][CH:19]=1>>[CH3:1][C:2]1([CH3:4])[O:8][C@@H:7]([C@H:9]2[O:10][C@@H:15]3[O:16][C:20]([CH3:21])([CH3:19])[O:14][C@@H:13]3[C@H:11]2[OH:12])[CH2:6][O:3]1

참가 물질

5

반응물 4

HCID 180AcetoneHCID 1049PyridineHCID 24841Hydrogen iodideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

생성물 1

HCID 7067560Diacetone-D-glucose수율 80%

반응 조건

온도
60 °C

실험 절차

To 200 ml of acetone were added 10.0 g of D-glucose and 100 mg of hydrogen iodide and the mixture was refluxed with stirring in a water bath at 60° C. for 8 hours. During this reaction, the refluxing solvent was dried with 20 g of Molecular Sieves 3A interposed between the reaction vessel and the cooling jacket. After completion of the reaction, a small amount of pyridine was added. The acetone was then distilled off under reduced pressure and the residue was dissolved in benzene, washed with aqueous sodium bicarbonate and water and dried over anhydrous magnesium sulfate. The benzene was distilled off under reduced pressure to give 11.5 g (80.0%) of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose. After recrystallization from chloroform-hexane (1:2), it melted at 107°-109° C.

후처리

  1. temperaturethe mixture was refluxed
  2. customDuring this reaction
  3. dry with materialthe refluxing solvent was dried with 20 g of Molecular Sieves 3A
  4. customAfter completion of the reaction
  5. distillationThe acetone was then distilled off under reduced pressure
  6. dissolutionthe residue was dissolved in benzene
  7. washwashed with aqueous sodium bicarbonate and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe benzene was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-6eda1e8c119c4ad88b58cba32bd75600
출처 데이터셋
uspto-grants-1984_08
특허 번호
US04464530

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