HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Propanol → (3S,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Propanol | HCID 1031 | — |
| Reactant | (4S,5S)-5-(Acetyloxymethyl)-4-[1,3]dioxolan-2-yldihydrofuran-2-one | HCID 11401953 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | (2S,3S)-3-[1,3]dioxolan-2-ylpentane-1,2,5-triol | HCID 69747925 | — |
| Catalyst | (2S,3S)-3-[1,3]dioxolan-2-ylpentane-1,2,5-triol | HCID 69747925 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Ether tetrahydrofuran | HCID 21868444 | — |
| Solvent | Oxolane--water (1/1) | HCID 21881883 | — |
| Product | (3S,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol | HCID 11147731 | 64% |
Reaction Steps
According to the above general procedure, a solution containing 1.44 mg (6.26 mmol) (4S,5S)-5-(acetyloxymethyl)-4-[1,3]dioxolan-2-yldihydrofuran-2-one (3c) in Et2O:THF 1:1 (20 mL) was reduced with 522 mg (13.75 mmol) LiAlH4 in Et2O (100 mL) to give the crude protected triol (4) (1.12 mg, 93%). The crude triol (4) was cyclized in 60 mL THF water (5:1) and 5 mL 1N hydrochloric acid. Column chromatography (silica gel 20 g, ethyl methanol in CHCl3 10%) gave compound (5) (515 mg, 64%) as a colorless solid, Rf=0.35, [α]25D −25.1°, c 1.0, MeOH.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06919465B2 |
| Source dataset | uspto-grants-2005_07 |
| ORD ID | ord-84eec643d5eb42329b5de8a4253cc083 |
| Source note | uspto-grants-2005_07 |