Sodium Bicarbonate → 4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-[2-(4-benzyloxycarbonylphenyl)ethyl]benzo[b]thiophene

HRID 230932Notes

Reaction equation

HRID 230932 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]2[C:20]3[C:27]([OH:28])=[CH:26][CH:25]=[CH:24][C:21]=3[S:22][CH:23]=2)=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([O:32][C@@H:33]1[C@@H:45]([O:46][C:47](=[O:49])[CH3:48])[C@H:44]([O:50][C:51](=[O:53])[CH3:52])[C@@H:43]([CH2:54][O:55][C:56](=[O:58])[CH3:57])[O:42][C@@H:34]1OC(=N)C(Cl)(Cl)Cl)(=[O:31])[CH3:30].C(=O)([O-])O.[Na+]>ClCCl>[C:29]([O:32][C@@H:33]1[C@@H:45]([O:46][C:47](=[O:49])[CH3:48])[C@H:44]([O:50][C:51](=[O:53])[CH3:52])[C@@H:43]([CH2:54][O:55][C:56](=[O:58])[CH3:57])[O:42][C@H:34]1[O:28][C:27]1[C:20]2[C:19]([CH2:18][CH2:17][C:14]3[CH:15]=[CH:16][C:11]([C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:10])=[CH:12][CH:13]=3)=[CH:23][S:22][C:21]=2[CH:24]=[CH:25][CH:26]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10896298alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate)HCID 231035283-[2-(4-Benzyloxycarbonylphenyl)ethyl]-4-hydroxybenzo[b]thiophene

Product 1

HCID 671365394-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-[2-(4-benzyloxycarbonylphenyl)ethyl]benzo[b]thiopheneYield 58.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[2-(4-benzyloxycarbonylphenyl)ethyl]-4-hydroxybenzo[b]thiophene (35 mg) and 2,3,4,6-tetra-O-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (53 mg) in dichloromethane (3 mL) was added boron trifluoride-diethyl ether complex (0.006 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1-3/2) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-[2-(4-benzyloxycarbonylphenyl)ethyl]benzo[b]thiophene (38 mg). This material was dissolved in dichloromethane (1 mL). To the solution were added dimethyl sulfide (0.15 mL) and boron trifluoride-diethyl ether complex (0.067 mL), and the mixture was stirred at 35° C. for 4 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=20/1) to give the title compound (25 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1-3/2)

Sources & evidence

ORD record
ord-80f182b5f8474f68805524f3c894aa8c
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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