Sodium Methoxide → 4-(beta-D-Glucopyranosyloxy)-3-(2-phenylethyl)benzo[b]-thiophene

HRID 230887ノート

反応式

HRID 230887 の反応式
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:33]2[C:32]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:31][S:30][C:29]=2[CH:28]=[CH:27][CH:26]=1)(=O)C.C[O-].[Na+]>CO>[C@@H:6]1([O:24][C:25]2[C:33]3[C:32]([CH2:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:31][S:30][C:29]=3[CH:28]=[CH:27][CH:26]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

参加物

4

反応物 2

HCID 10942334Sodium MethoxideHCID 671360454-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-(2-phenylethyl)benzo[b]thiophene

生成物 1

HCID 671362524-(beta-D-Glucopyranosyloxy)-3-(2-phenylethyl)benzo[b]-thiophene収率 78.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a suspension of 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-(2-phenylethyl)benzo[b]thiophene (75 mg) in methanol (3 mL) was added sodium methoxide (28% methanol solution, 0.025 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (42 mg).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

出典と根拠

ORDレコード
ord-458a8001c1874df6a3001836535ec454
出典データセット
uspto-grants-2009_07
特許番号
US07566699B2

反応ノート

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