HuagongsheHuagongshe Chemistry Print Report · For research reference only
(3aR,4R5R,6aS)-4-((S,E)-3-(tert-Butyldimethylsilyloxy)-5-phenylpent-1-enyl)-2-methoxyhexahydro-2H-cyclopenta[b]furan-5-ol → Silanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (3aR,4R5R,6aS)-4-((S,E)-3-(tert-Butyldimethylsilyloxy)-5-phenylpent-1-enyl)-2-methoxyhexahydro-2H-cyclopenta[b]furan-5-ol | HCID 131734562 | — |
| Solvent | HCl tetrahydrofuran | HCID 18422008 | — |
| Product | Silanol | HCID 142154 | — |
| Product | 2H-Cyclopenta[b]furan-2,5-diol, hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl 1-penten-1-yl]-, (3aR,4R,5R,6aS) | HCID 58700543 | — |
Reaction Steps
Alcohol 93 (210 mg, 0.485 mmol) was stirred with 1.5% aqueous HCl/THF (3:2) (10 ml) at r.t. for 16 h. The mixture was extracted with CH2Cl2 (5×15 ml) and the combined organic phases were dried (MgSO4), filtered, and concentrated to give the triol 94 and silanol by-product as a clear, colourless oil. This material was taken forward for the subsequent transformation without purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09242954B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-37fa9ac1678947b4b0f5eee9841178f9 |
| Source note | uspto-grants-2016_01 |