HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → (2S,3S,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-3-ethoxy-3-oxo-1-(3-(trifluoromethyl)phenyl)prop-1-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ethyl (3-trifluoromethylphenyl)pyruvate | HCID 18370921 | — |
| Reactant | (2S,3S,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-3-ethoxy-1-(2-fluorophenyl)-3-oxoprop-1-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | HCID 66980300 | — |
| Reactant | 2,3,4,6 tetra-O-acetyl-alpha-D-glucose bromide | HCID 86702362 | — |
| Product | (2S,3S,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-3-ethoxy-3-oxo-1-(3-(trifluoromethyl)phenyl)prop-1-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | HCID 68030652 | 22% |
Reaction Steps
The title compound was prepared as described for C4 using ethyl 3-(3-(trifluoromethyl)phenyl)-2-oxopropanoate B10 (100 mg, 0.384 mmol), sodium hydride (10.14 mg, 0.544 mmol) and 2,3,4,6-tetra-O-acetyl-α-D-glucose bromide (158 mg, 0.384 mmol). The resulting compound was isolated in the form of white solid in 22% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09221860B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-249f16327ca34aef8702ae9b4b9b4c82 |
| Source note | uspto-grants-2015_12 |