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

HRID 15412노트

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HRID 15412 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[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]

참가 물질

5

반응물 3

HCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 68714543HCID 68714543, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a0615df7fb9943238736a4156d6b0da8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732596B2

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