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Triacetoxyperiodinane → (4aR,6aR,11aR,11bR)-7,9-Dimethoxy-4,4,6a,11b-tetramethyl-1,2,4,4a,5,6,6a,11,11a,11b-decahydro-benzo[a]fluoren-3-one

HRID 1466728
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HRID 1466728 반응식
[CH3:1][O:2][C:3]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]2[C:4]=1[C@@:5]1([CH3:26])[C@H:10]([CH2:11]2)[C@@:9]2([CH3:25])[CH2:18][CH2:19][C@H:20]([OH:24])[C:21]([CH3:23])([CH3:22])[C@@H:8]2[CH2:7][CH2:6]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]2[C:4]=1[C@@:5]1([CH3:26])[C@H:10]([CH2:11]2)[C@@:9]2([CH3:25])[CH2:18][CH2:19][C:20](=[O:24])[C:21]([CH3:22])([CH3:23])[C@@H:8]2[CH2:7][CH2:6]1
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참가 물질

5

반응물 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 56837778(3S,4aR,6aR,11aR,11bR)-7,9-Dimethoxy-4,4,6a,11b-tetramethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluoren-3-ol

생성물 1

HCID 56837781(4aR,6aR,11aR,11bR)-7,9-Dimethoxy-4,4,6a,11b-tetramethyl-1,2,4,4a,5,6,6a,11,11a,11b-decahydro-benzo[a]fluoren-3-one수율 80.2%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To alcohol 5b (600 mg, 1.67 mmol) dissolved in 85 mL of methylene chloride was added Dess-Martin periodinane (DMP, 1.41 g, 3.34 mmol), and the mixture was allowed to stir at room temperature for 1.5 hours. Upon reaction completion, saturated aqueous NaHCO3 (50 mL) was added and the aqueous phase was extracted 3 times with methylene chloride (3×50 mL). The organic extracts were then combined, dried with MgSO4, and concentrated. The crude mixture was purified using flash chromatography (hexanes:ethyl acetate 7:1) to give 6b (476 mg, 1.34 mmol, 80% yield) as a white crystalline solid. 1H NMR (400 MHz, CDCl3) δ 6.41 (s, 1H), 6.27 (s, 1H), 3.77 (s, 3H), 3.75 (s, 3H), 2.71-2.65 (m, 1H), 2.64-2.56 (m, 2H), 2.54-2.41 (m, 2H), 1.87-1.81 (m, 1H), 1.78-1.73 (m, 2H), 1.71-1.48 (m, 4H), 1.13 (s, 3H), 1.11 (s, 6H), 1.09 (s, 3H); 13C NMR (100 MHz, CDCl3) δ217.2, 159.5, 155.8, 144.4, 132.9, 101.9, 96.8, 63.4, 55.4, 55.3, 54.9, 47.5, 45.8, 38.8, 37.4, 36.2, 33.9, 29.5, 26.5, 20.7, 20.5, 19.8, 15.5. ESIMS [M+Na]+ calcd for C23H32O3Na 379.2249, found 379.2243. [α]24D=+26.78°.

후처리

  1. additionwas added
  2. extractionthe aqueous phase was extracted 3 times with methylene chloride (3×50 mL)
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. customThe crude mixture was purified

출처 및 근거

ORD 기록
ord-6e251b17c48e44dc988e5e61fda1fcfb
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09000050B2

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