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

HRID 39610

反応式

HRID 39610 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-29b210fe04f64a8496c8e49b01ed12b9
出典データセット
uspto-grants-2013_09
特許番号
US08524939B2

関連ノート

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