HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → (2S,3R,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-3-methoxy-3-oxo-1-(thiophen-2-yl)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 | Methyl 2-oxo-3-(2-thienyl)propionate | HCID 20277529 | — |
| 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-methoxy-3-oxo-1-(thiophen-2-yl)prop-1-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | HCID 66980233 | 23% |
Reaction Steps
The title compound was prepared as described for C4 using methyl 2-oxo-3-(thiophen-2-yl)propanoate B13 (Otava, 100 mg, 0.543 mmol), sodium hydride (13.03 mg, 0.373 mmol) and 2,3,4,6-tetra-O-acetyl-α-D-galactose bromide (223 mg, 0.543 mmol). The compound was isolated in the form of white solid in 23% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09221860B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-96c7f623396a44e7aff76e8a8517d3ad |
| Source note | uspto-grants-2015_12 |