ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

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
ノート
印刷プレビュー

反応式

HRID 1466728 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 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-one収率 80.2%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-6e251b17c48e44dc988e5e61fda1fcfb
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09000050B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート