HuagongsheHuagongshe Chemistry Print Report · For research reference only
(25R)-16beta-HYDROXY-26-PHTHALIMIDOCHOLESTEROL → (25R)-16-oxo-26-phthalimidocholesterol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (25R)-16beta-HYDROXY-26-PHTHALIMIDOCHOLESTEROL | HCID 10962631 | — |
| Reactant | Phthalimide potassium salt | HCID 24194345 | — |
| Product | (25R)-16-oxo-26-phthalimidocholesterol | HCID 9832896 | — |
Reaction Steps
According to Scheme 1, (25R)-16β-26-dihydroxycholesterol (2), prepared in one step from diosgenin, is selectively reacted at the C-26 hydroxyl group with p-toluene sulfonyl chloride to yield (25R)-16β-26-dihydroxycholesterol 26-tosylate (3) which is then reacted with potassium phthalimide. The resulting (25R)-16β-hydroxy-26-phthalimidocholesterol (4) is then subjected to a modified Jones oxidation which selectively oxidizes the 16β hydroxy group to form (25R)-16-oxo-26-phthalimidocholesterol (5).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05274088 |
| Source dataset | uspto-grants-1993_12 |
| ORD ID | ord-bd6166ee32c64e11b58eb13b7ae978b3 |
| Source note | uspto-grants-1993_12 |