Hydrogen Peroxide → 4-(beta-D-glucopyranos-1-yl)-2-(4-methylsulfinyl-benzyl)-benzonitrile

HRID 19838

反応式

HRID 19838 の反応式
[OH:1]O.[OH:3][C@:4]1([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([S:30][CH3:31])=[CH:26][CH:25]=3)[CH:16]=2)[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6]>O.C(O)(C(F)(F)F)C(F)(F)F>[OH:3][C@:4]1([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([S:30]([CH3:31])=[O:1])=[CH:28][CH:29]=3)[CH:16]=2)[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6]

参加物

5

反応物 2

HCID 784Hydrogen PeroxideHCID 866189584-(beta-D-glucopyranos-1-yl)-2-(4-methylsulfanyl-benzyl)-benzonitrile

生成物 1

HCID 866189574-(beta-D-glucopyranos-1-yl)-2-(4-methylsulfinyl-benzyl)-benzonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 135291,1,1,3,3,3-Hexafluoro-2-propanol溶媒

実験手順

35% Hydrogen peroxide in water (48 μL) is added to 4-(β-D-glucopyranos-1-yl)-2-(4-methylsulfanyl-benzyl)-benzonitrile (83 mg) in 1,1,1,3,3,3-hexafluoroisopropanol (2 mL). The resulting solution is stirred at ambient temperature for 1 h and then quenched by the addition of aqueous Na2S2O3 solution and aqueous NaHCO3 solution. The organic phase is separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->5:1).

後処理

  1. customquenched by the addition of aqueous Na2S2O3 solution and aqueous NaHCO3 solution
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customthe solvent is removed
  6. customThe residue is chromatographed on silica gel (dichloromethane/methanol 1:0->5:1)

出典と根拠

ORDレコード
ord-935f5aedee184cb99a23d3432b7a09be
出典データセット
uspto-grants-2010_06
特許番号
US07745414B2

関連ノート

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