Ethanethiol → 2-(beta-D-Glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiophene

HRID 15412ノート

反応式

HRID 15412 の反応式
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@H:10]1[C:40]1[S:44][C:43]2[C:45]([CH2:49][C:50]3[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=3)=[CH:46][CH:47]=[CH:48][C:42]=2[CH:41]=1)C1C=CC=CC=1.C(S)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C@@H:10]1([C:40]2[S:44][C:43]3[C:45]([CH2:49][C:50]4[CH:51]=[CH:52][C:53]([CH3:56])=[CH:54][CH:55]=4)=[CH:46][CH:47]=[CH:48][C:42]=3[CH:41]=2)[O:11][C@H:12]([CH2:31][OH:32])[C@@H:13]([OH:23])[C@H:14]([OH:15])[C@H:9]1[OH:8]

参加物

5

反応物 3

HCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 68714543HCID 68714543、化合物

生成物 1

HCID 117499522-(beta-D-Glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiophene収率 32%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiophene (0.95 g) and ethanethiol (1.8 mL) in dichloromethane (15 mL) was added boron trifluoride diethyl ether complex (2.1 mL) at room temperature. The reaction mixture was stirred at room temperature for 3 hours, and a saturated potassium carbonate aqueous solution was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (0.16 g).

後処理

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. 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-a0615df7fb9943238736a4156d6b0da8
出典データセット
uspto-grants-2010_06
特許番号
US07732596B2

反応ノート

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