참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Ethyl Acetate | HCID 8857 | — |
| 반응물 | Sodium Acetate | HCID 517045 | — |
| 반응물 | (3S,8S,9S,10R,13S,14S,16S,17R)-17-[(1R,5R)-6-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol | HCID 11729441 | — |
| 촉매 | chromium (VI) trioxide | HCID 10219390 | — |
| 용매 | Acetic Acid | HCID 176 | — |
| 용매 | Water | HCID 962 | — |
| 생성물 | (25R)-16-oxo-26-hydroxycholesterol | HCID 13873472 | 62.9% |
반응 단계
A solution of chromium trioxide (80 mg) in water (0.4 ml) and acetic acid (0.8 ml) is added dropwise to a solution of (25R)-16β,26-dihydroxycholesterol (2) (0.500 g), and sodium acetate (2.48 g) in glacial acetic acid (90 ml), and is stirred for 18 hours at room temperature. The excess reagent is then destroyed with methanol (15 ml), and solvent is evaporated under reduced pressure. The resulting residue is diluted with water, and extracted with methylene chloride. The organic layer is washed with 5% K2CO3 and water, dried over sodium sulfate, and evaporated under reduced pressure to yield 0.48 g of crude product. The mixture is resolved by silica flash column chromatography (hexanes:ethyl acetate) to afford 0.313 g of (25R)-16-oxo-26-hydroxycholesterol (9). M.pt. 167°-169° C.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US05274088 |
|---|
| 출처 데이터셋 | uspto-grants-1993_12 |
|---|
| ORD ID | ord-d41089aefb8840d7900b79b66001bbf6 |
|---|
| 출처 메모 | uspto-grants-1993_12 |
|---|
