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Water → D-Glucitol, 1,5-anhydro-1-C-[5-(2-azulenylmethyl)-2-hydroxyphenyl]-, (1S)-

HRID 1376006
ノート
印刷プレビュー

反応式

HRID 1376006 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].C1(OC)C=CC=CC=1.[CH:13]1[C:22]2[C:16]([CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:15][C:14]=1[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:69]CC2C=CC=CC=2)=[C:28]([C@@H:30]2[O:59][C@H:58]([CH2:60][O:61]CC3C=CC=CC=3)[C@@H:49]([O:50]CC3C=CC=CC=3)[C@H:40]([O:41]CC3C=CC=CC=3)[C@H:31]2[O:32]CC2C=CC=CC=2)[CH:29]=1.O>C(Cl)Cl>[CH:13]1[C:22]2[C:16]([CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:15][C:14]=1[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([OH:69])=[C:28]([C@@H:30]2[O:59][C@H:58]([CH2:60][OH:61])[C@@H:49]([OH:50])[C@H:40]([OH:41])[C@H:31]2[OH:32])[CH:29]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 11535213HCID 11535213、化合物

生成物 1

HCID 11560307D-Glucitol, 1,5-anhydro-1-C-[5-(2-azulenylmethyl)-2-hydroxyphenyl]-, (1S)-収率 30.5%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

Aluminum chloride (0.12 g) and anisole (4.0 ml) were added to a solution of (1S)-1,5-anhydro-1-[5-(azulen-2-ylmethyl)-2-(benzyloxy)phenyl]-2,3,4,6-tetra-O-benzyl-D-glucitol (0.07 g) in methylene chloride (5 ml) and the mixture was stirred at room temperature for two hours. The reaction mixture was poured into ice-cooled water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain (1S)-1,5-anhydro-1-[5-(azulen-2-ylmethyl)-2-hydroxyphenyl]-D-glucitol (0.01 g).

後処理

  1. additionThe reaction mixture was poured into ice-
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

出典と根拠

ORDレコード
ord-4f37995bf11d4aff81cb68901685cf40
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07169761B2

反応ノート

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