HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,6-Di-O-(p-toluenesulphonyl)-2,5-anhydro-D-mannitol → (2R,3S,4S,5R)-2,5-dimethyltetrahydrofuran-3,4-diol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,6-Di-O-(p-toluenesulphonyl)-2,5-anhydro-D-mannitol | HCID 14076916 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (2R,3S,4S,5R)-2,5-dimethyltetrahydrofuran-3,4-diol | HCID 11105400 | — |
Reaction Steps
0.86 g (22.66 mmol) of LiAlH4 was added to a solution of 3.60 g (7.63 mmol) of B3 in 20 ml of anhydrous THF and stirred at reflux for 2 hours. After cooling, Arberlite® IR-120(plus) was added and stirring was continued until hydrogen evolution had ended. The mixture was filtered through Celite® and the solvent was subsequently removed under reduced pressure. The crude product was purified by means of column chromatography (CH2Cl2/MeOH=12:1). Yield: 0.84 g (84% of theory).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07193092B2 |
| Source dataset | uspto-grants-2007_03 |
| ORD ID | ord-b11d81f910544e3dbcb02dbf9a8f8ec2 |
| Source note | uspto-grants-2007_03 |