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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Naphthalene → (1S,2RS,5S,6S,7R)-2-hydroxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane

HRID 1974774
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HRID 1974774 반응식
CS(O[CH2:6][C:7]12[O:39][CH:8]1[C@@H:9]1[C@H:13]([CH2:14]2)[C@H:12](/[CH:15]=[CH:16]/[C@@H:17]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:11]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:10]1)(=O)=O.C1C2C(=CC=CC=2)C=CC=1.[Na].[Cl-].[NH4+]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[OH:39][CH:8]1[C:7](=[CH2:6])[CH2:14][C@H:13]2[C@@H:9]1[CH2:10][C@@H:11]([O:31][Si:32]([C:35]([CH3:36])([CH3:38])[CH3:37])([CH3:33])[CH3:34])[C@H:12]2/[CH:15]=[CH:16]/[C@@H:17]([O:23][Si:24]([C:27]([CH3:28])([CH3:29])[CH3:30])([CH3:25])[CH3:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]
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참가 물질

7

반응물 4

HCID 931NaphthaleneHCID 25517Ammonium Chloride2회HCID 5360545SodiumHCID 22850329(1S,2RS,-3RS,5S,6S,7R)-3-methanesulfonyloxymethyl-2,3-epoxy-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane

생성물 1

HCID 13955240(1S,2RS,5S,6S,7R)-2-hydroxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane
수율 78.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 21226206Ethyl acetate hexane용매

실험 절차

A solution of 917 mg (1.52 mmoles) of (1S,2RS,-3RS,5S,6S,7R)-3-methanesulfonyloxymethyl-2,3-epoxy-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane obtained in Example 2 in 3 ml of tetrahydrofuran was added to an anion radical solution prepared by reacting naphthalene (1.28 g, 10 mmoles) with sodium (207 mg, 9 mmoles) in 30 ml of tetrahydrofuran at room temperature for I hour. The mixture was stirred at room temperature for 10 minutes and 3.0 g of ammonium chloride was added to the reaction solution. Then, a saturated aqueous solution of ammonium chloride was added and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give a crude product. It was subjected to column chromatography (silica gel 50 g; hexane/ethyl acetate=19/1) to give (1S,2RS,5S,-6S,7 R)-2-hydroxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy- 1-octenyl) -7-t-butyldimethylsilyloxybicyclo[3.3.0]octane (605 mg, 1.19 mmoles, 78%).

후처리

  1. customprepared
  2. customat room temperature
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give a crude product

출처 및 근거

ORD 기록
ord-620689bb402e442caf16beae770c4586
출처 데이터셋
uspto-grants-1994_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05283349

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