HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → (2S,3R,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-3-ethoxy-3-oxo-1-phenylprop-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 2-oxo-3-phenylpropanoate | HCID 12292599 | — |
| 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-galactose bromide | HCID 86702363 | — |
| Product | (2S,3R,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-3-ethoxy-3-oxo-1-phenylprop-1-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | HCID 66980174 | 37% |
Reaction Steps
The title compound was prepared as described for C4 using (ethyl 3-(phenyl)-2-oxopropanoate B6 (100 mg, 0.520 mmol), sodium hydride (13.73 mg, 0.572 mmol) and 2,3,4,6-tetra-O-acetyl-α-D-galactose bromide (214 mg, 0.520 mmol). The resulting compound was isolated in the form of white solid in 37% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09221860B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-fa321faceacc44f0b2f1466575e043e1 |
| Source note | uspto-grants-2015_12 |