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Hydrogen Peroxide → 4-(3-{3-(Tert-butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-hydroxy-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester

HRID 1393696
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HRID 1393696 반응식
[CH3:1][O:2][C:3](=[O:48])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[C:17](=[O:18])[CH2:16][CH:15]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:14]2[CH:27]=[CH:28][CH:29]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH:30]([CH3:35])[CH2:31][C:32]#[C:33][CH3:34])[C:8]=1[O:44][CH2:45][O:46][CH3:47].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].OO>C1COCC1>[CH3:1][O:2][C:3](=[O:48])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[CH:17]([OH:18])[CH2:16][CH:15]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:14]2[CH:27]=[CH:28][CH:29]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH:30]([CH3:35])[CH2:31][C:32]#[C:33][CH3:34])[C:8]=1[O:44][CH2:45][O:46][CH3:47]
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참가 물질

5

반응물 3

HCID 784Hydrogen PeroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 69215476HCID 69215476, 화합물

생성물 1

HCID 692154174-(3-{3-(Tert-butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-hydroxy-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester수율 90%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
-78 °C

실험 절차

4-(3-{3-(tert-Butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-oxo-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester of 2.6 g (3.67 mmol) was dissolved in THF (40 ml). The solution was cooled to −78° C., and then, L-selectride (1 M.THF solution, 7.35 mmol) was slowly added thereto dropwise. The mixture was stirred at the above temperature for 2 hours, and the reaction was stopped with hydrogen peroxide (30% aqueous solution, 16 mmol). The reaction solution was stirred at 0° C. for 30 minutes, and then, extracted with diethyl ether. The combined organic layer was washed with water and brine, and then, dried over magnesium sulfate, filtered off, and concentrated under reduced pressure. The concentrate was subjected to column chromatography on a silica gel (hexane:ethyl acetate=4:1) to obtain 4-(3-{3-(tert-butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-hydroxy-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester (2.3 g, yield: 90%).

후처리

  1. stirringThe reaction solution was stirred at 0° C. for 30 minutes
  2. extractionextracted with diethyl ether
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0aceb9f746ab4c28907b3a584e16b1f9
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07345181B2

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