HuagongsheHuagongshe Chemistry Print Report · For research reference only
((2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxotetrahydro-2H-pyran-2-yl)methyl acetate → (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-tetrahydropyran-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | ((2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxotetrahydro-2H-pyran-2-yl)methyl acetate | HCID 16113281 | — |
| Catalyst | Tin atom | HCID 5352426 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-tetrahydropyran-2-one | HCID 10659025 | 30% |
Reaction Steps
((2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxotetrahydro-2H-pyran-2-yl)methyl acetate (VI) (0.625 g, 80% purity, 1.65 mmol) was dissolved in THF (8 mL) and MeOH (8 mL). Tin catalyst (tBu2SnClOH)2 (94 mg, 0.1 eq) was added and the reaction was stirred overnight. Reaction was concentrated and purified by flash chromatography to give pure (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one (VII) (126 mg, 30%). VII was found to contain less than 0.1% of enantiomer.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08404870B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-32dbba9c7c334c15bf91feffaf6c3c98 |
| Source note | uspto-grants-2013_03 |