Hydrogen Peroxide → ((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(tert-butyldimethylsilyloxy)-3-((S)-3-(tert-butyldimethylsilyloxy)octyl)cyclopentyl)methanol

HRID 39610

반응식

HRID 39610 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:43]=[CH:44][CH:45]=1)[CH2:12][C@H:13]1[C:17](=[CH2:18])[CH2:16][C@@H:15]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C@@H:14]1[CH2:27][CH2:28][C@@H:29]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C12BC(CCC1)CCC2.[OH:55]O.[OH-].[K+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:43]=[CH:44][CH:45]=1)[CH2:12][C@@H:13]1[C@@H:14]([CH2:27][CH2:28][C@@H:29]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:37])[CH3:38])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C@H:15]([O:19][Si:20]([C:23]([CH3:25])([CH3:26])[CH3:24])([CH3:21])[CH3:22])[CH2:16][C@@H:17]1[CH2:18][OH:55])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 86677378((1R,2R,3R)-3-(3-(benzyloxy)benzyl)-2-((S)-3-(tert-butyldimethylsilyloxy)octyl)-4-methylenecyclopentyloxy)(tert-butyl)dimethylsilane

생성물 1

HCID 71268547((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(tert-butyldimethylsilyloxy)-3-((S)-3-(tert-butyldimethylsilyloxy)octyl)cyclopentyl)methanol수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A degassed solution of ((1R,2R,3R)-3-(3-(benzyloxy)benzyl)-2-((S)-3-(tert-butyldimethylsilyloxy)octyl)-4-methylenecyclopentyloxy)(tert-butyl)dimethylsilane (0.75 g, 1.15 mmol) in 8 ml dry THF was cooled to 0° C. under nitrogen, and 9-borabicyclo[3,3,1]nonane (6.9 ml, 0.5M in THF) was dropwise added to the mixture. The colorless solution was stirred for overnight at 0° C. and treated with 30% hydrogen peroxide (3 ml) followed by 3N potassium hydroxide (3 ml). The resulting suspension was stirred for one hour at room temperature. The mixture was extracted with EtOAc, and the organic layer was washed with 20 ml brine, dried over MgSO4, and evaporated. The resulting residue was purified by chromatography on a silica gel column using hexane-EtOAc as eluent to give the titled compound: 0.6 g (yield 78%)

후처리

  1. stirringThe resulting suspension was stirred for one hour at room temperature
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layer was washed with 20 ml brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe resulting residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-29b210fe04f64a8496c8e49b01ed12b9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524939B2

연결된 노트

불러오는 중…