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

HRID 15407

반응식

HRID 15407 반응식
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[CH:45]=[CH:46][CH:47]=[C:48]([CH2:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[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[CH:45]=[CH:46][CH:47]=[C:48]([CH2:49][CH2:50][C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[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]

참가 물질

5

실험 절차

To a solution of 2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4-(2-phenylethyl)benzo[b]thiophene (0.58 g) and ethanethiol (1.13 mL) in dichloromethane (10 mL) was added boron trifluoride diethyl ether complex (1.43 mL) at room temperature, and the mixture was stirred for 3 hours. A saturated potassium carbonate aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (94 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract 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)

출처 및 근거

ORD 기록
ord-d242b309769541cd9bdfd13e8f2903ab
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732596B2

연결된 노트

불러오는 중…