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m-Chloroperbenzoic acid → (1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-8-one

HRID 422136
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HRID 422136 반응식
[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]2[C:4]=1[C@@:5]1([CH3:26])[C@H:14]([CH2:15][S:16]2)[C@:13]2([CH3:23])[C@H:8]([C:9]([CH3:25])([CH3:24])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1.ClC1C=C(C=CC=1)C(OO)=[O:32]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]2[C:4]=1[C@@:5]1([CH3:26])[C@H:14]([CH2:15][S:16]2=[O:32])[C@:13]2([CH3:23])[C@H:8]([C:9]([CH3:25])([CH3:24])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1
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참가 물질

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반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 53241775(1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene

생성물 1

HCID 53241883(1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-8-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene (Compound No. 22) (187 mg, 0.5 mmol) in CH2Cl2 (20 mL) was added 3-chloroperoxybenzoic acid (77%, 112 mg, 0.5 mmol) portionwise at room temperature. The resulting mixture was stirred at room temperature for 2 h. CH2Cl2 (100 mL) was added and the mixture washed with saturated aqueous sodium bicarbonate (20 mL), dried (Na2SO4), and concentrated. Purification by chromatography on silica gel (Hexanes/EtOAc, 1:1) gave (1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-8-one (Compound No. 24) as separate diastereomers. (Diastereomer 1, white foam, 44 mg; Diastereomer 2, white solid, 290 mg).

후처리

  1. washthe mixture washed with saturated aqueous sodium bicarbonate (20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification by chromatography on silica gel (Hexanes/EtOAc, 1:1)

출처 및 근거

ORD 기록
ord-dee375813c2547f7859b141065e97f3b
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08101605B2

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