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(1R,4S)-4-((tert-Butyldimethylsilyl)oxy)cyclopent-2-en-1-ol → (1R,4R)-4-((tert-Butyldimethylsilyl)oxy)cyclopent-2-en-1-ol

HRID 2180025
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인쇄 미리보기

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HRID 2180025 반응식
[OH:1][C@H:2]1[CH:6]=[CH:5][C@@H:4]([O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])[CH2:3]1>CCOC(C)=O.CCCCCC>[O:7]([C@H:4]1[CH:5]=[CH:6][C@H:2]([OH:1])[CH2:3]1)[Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]
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참가 물질

3

반응물 1

HCID 10910904(1R,4S)-4-((tert-Butyldimethylsilyl)oxy)cyclopent-2-en-1-ol

생성물 1

HCID 10878531(1R,4R)-4-((tert-Butyldimethylsilyl)oxy)cyclopent-2-en-1-ol수율 81%

시약·촉매·용매 1

HCID 21226206Ethyl acetate hexane용매

실험 절차

Compound 14 was subjected to general procedure J. Yield=81%. TLC: Rf=0.50 (10% EtOAc/Hexane). 1H NMR (400 MHz, CDCl3): δ0.05 (s, 6H), 0.90 (s, 9H), 2.20 (m, 1H), 2.30 (m, 1H), 5.10 (s, 1H), 6.05 (m, 2H), 6.10 (m, 1H), 8.20 (d, 2H), 8.20 (d, 2H). Subsequent subjection of the product to general procedure E gave compound 22. Yield=85%. TLC: Rf=0.33 (25% EtOAc/Hexane). 1H NMR (400 MHz, CDCl3): δ0.05 (s, 6H), 0.90 (s, 9H), 2.05 (m, 2H), 5.00 (m, 1H), 5.05 (m, 1H), 5.95 (m, 2H).

출처 및 근거

ORD 기록
ord-ada8f3ba0ee247e8815f310e840cabe8
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06887880B2

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