Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | HCID 66765962 | HCID 66765962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 13845546 | HCID 13845546 | 66.3% |
Reaction Steps
To a solution of 1-(2,4-dimethoxyphenyl)-2,3,4,6-tetra-O-benzyl-D-glucopyranose (1.7 g) and triethylsilane (0.59 g) in acetonitrile (20 mL) was added boron trifluoride diethyl ether complex (0.40 g) under ice-cooling, and the mixture was warmed to room temperature and stirred overnight. A saturated potassium carbonate aqueous solution was added to the reaction mixture, and the mixture was stirred for 30 minutes. The mixture was poured into water, and the mixture was extracted with diethyl ether. The organic layer washed with water and 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: n-hexane/ethyl acetate=6/1) to give the title compound (1.1 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08058245B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-d65dbd748b394b6fae29d5162d117624 |
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| Source note | uspto-grants-2011_11 |
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