Dimethyl Sulfide → (-)-4'-Demethylepipodophyllotoxin

HRID 1686180노트

반응식

HRID 1686180 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:13]2[C@H:22]3[C:23]([O:25][CH2:26][C@@H:21]3[C@@H:20]([OH:27])[C:19]3[CH:18]=[C:17]4[O:28][CH2:29][O:30][C:16]4=[CH:15][C:14]2=3)=[O:24])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9]C.CS(O)(=O)=O.CSC>FC(F)(F)C(O)=O>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C@H:13]2[C@H:22]3[C:23]([O:25][CH2:26][C@@H:21]3[C@H:20]([OH:27])[C:19]3[CH:18]=[C:17]4[O:28][CH2:29][O:30][C:16]4=[CH:15][C:14]2=3)=[O:24])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[OH:9]

참가 물질

5

반응물 3

HCID 1068Dimethyl SulfideHCID 6395Methanesulfonic AcidHCID 10607Podophyllotoxin

생성물 1

HCID 122797(-)-4'-Demethylepipodophyllotoxin수율 65,562,924%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

10 g (24 nmol) of podophyllotoxin are dissolved in 60 ml of trifluoroacetic acid. There are successively added 5.4 ml (72 mmol) of methanesulfonic acid. Stirring is carried out for 9 hours, 5.4 ml (72 mmol) of dimethyl sulfide are again added and stirring is carried out for 9 hours. The mixture is discharged onto ice (600 ml) and extracted with ethyl acetate (3×300 ml). The organic phases are washed with water and then with NaHCO3 solution until neutral. After drying over sodium sulfate, filtration and evaporation, there are obtained 6.3 g of 4′-demethylepipodophyllotoxin, which is used directly in the next step.

후처리

  1. stirringstirring
  2. waitis carried out for 9 hours
  3. extractionextracted with ethyl acetate (3×300 ml)
  4. washThe organic phases are washed with water
  5. dry with materialAfter drying over sodium sulfate, filtration and evaporation, there

출처 및 근거

ORD 기록
ord-f6c7af2217ec4cd5aeb26406552151b5
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148552B2

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