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[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[(4-bromophenyl)methyl]-4-methyl-indolin-1-yl]tetrahydropyran-2-yl]methyl acetate → 3-(4-bromophenylmethyl)-4-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

HRID 2284526
ノート
印刷プレビュー

反応式

HRID 2284526 の反応式
[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[CH:26]([CH2:34][C:35]3[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][CH:36]=3)[CH2:25]2)[O:7]1)(=[O:3])[CH3:2]>ClCCl.[O-2].[Mn+4].[O-2]>[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[C:26]([CH2:34][C:35]3[CH:36]=[CH:37][C:38]([Br:41])=[CH:39][CH:40]=3)=[CH:25]2)[O:7]1)(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

HCID 118021460[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[(4-bromophenyl)methyl]-4-methyl-indolin-1-yl]tetrahydropyran-2-yl]methyl acetate

生成物 1

HCID 671974083-(4-bromophenylmethyl)-4-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole収率 67.9%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

Add manganese (IV) oxide (172.5 mmol) to a solution of [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[(4-bromophenyl)methyl]-4-methyl-indolin-1-yl]tetrahydropyran-2-yl]methyl acetate (5.85 mmol) in dichloromethane (20 mL). Stir at room temperature for 48 hours. Filter the reaction through diatomaceous earth and concentrate under reduced pressure. Treat the crude product with dichloromethane/methanol (30 mL of 10:1) and stir for 15 minutes. Filter the resulting precipitate and rinse the filter cake with methanol (2×10 mL). Dry the filter cake under vacuum to yield the title compound as a colorless solid (2.5 g 3.97 mmol): MS (m/z): 630 (M+H).

後処理

  1. filtrationFilter
  2. customthe reaction through diatomaceous earth
  3. concentrationconcentrate under reduced pressure
  4. additionTreat the crude product with dichloromethane/methanol (30 mL of 10:1)
  5. stirringstir for 15 minutes
  6. filtrationFilter the resulting precipitate
  7. washrinse the filter cake with methanol (2×10 mL)
  8. customDry the filter cake under vacuum

出典と根拠

ORDレコード
ord-9b815b3661f04e118ab10f29d177ec91
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09145435B2

反応ノート

読み込み中…

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