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

HRID 230922Notes

Reaction equation

HRID 230922 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:23]3[C:24]([OH:28])=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][CH:20]=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(OCC)(=O)C>[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:24]1[C:23]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:20][O:21][C:22]=2[CH:27]=[CH:26][CH:25]=1)(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 10896298alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate)HCID 67135888HCID 67135888, compound

Product 1

HCID 671358824-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-[2-(4-benzyloxycarbonylphenyl)ethyl]-benzofuranYield 89.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[2-(4-Benzyloxycarbonylphenyl)ethyl]-4-hydroxybenzofuran (0.26 g) and 2,3,4,6-tetra-O-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (0.41 g) were dissolved in dichloromethane (5 mL)-ethyl acetate (3 mL). To the solution was added boron trifluoride-diethyl ether complex (0.44 mL), and the mixture was stirred at room temperature for 3 hours. 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=3/2-2/3) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-[2-(4-benzyloxycarbonylphenyl)ethyl]-benzofuran (0.44 g). This material was dissolved in tetrahydrofuran (5 mL). To the solution was added 10% palladium-carbon powder (0.2 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 1 hour. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (0.37 g).

Workup

  1. additionTo the solution was added boron trifluoride-diethyl ether complex (0.44 mL)
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/2-2/3)

Sources & evidence

ORD record
ord-1b17179499f04d5ba77edf198a93a156
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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