Ethanethiol → 2-(beta-D-Glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiophene
Reaction equation
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]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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).
Workup
- extractionThe mixture was extracted with ethyl acetate
- washThe organic layer washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed under reduced pressure
- customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)
Sources & evidence
- ORD record
- ord-a0615df7fb9943238736a4156d6b0da8
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732596B2
Reaction notes
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