1alpha,3beta-Diacetoxy-ergosta-5,7,22-trien → Doxercalciferol

HRID 845358

反応式

HRID 845358 の反応式
C([O:4][C@@H:5]1[C@@:30]2([CH3:31])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:29]2[CH2:28][CH2:27][C@@:26]2([CH3:32])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:25])[CH:18]=[CH:19][C@H:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])[CH2:8][C@@H:7]([O:33]C(=O)C)[CH2:6]1)(=O)C>CCOCC>[CH3:25][C@@H:17]([C@@H:16]1[C@@:26]2([CH3:32])[CH2:27][CH2:28][CH2:29]/[C:12](=[CH:11]\[CH:10]=[C:9]3\[CH2:8][C@@H:7]([OH:33])[CH2:6][C@H:5]([OH:4])[C:30]\3=[CH2:31])/[C@@H:13]2[CH2:14][CH2:15]1)/[CH:18]=[CH:19]/[C@@H:20]([CH:21]([CH3:22])[CH3:23])[CH3:24]

参加物

3

反応物 1

HCID 543403811alpha,3beta-Diacetoxy-ergosta-5,7,22-trien

生成物 1

HCID 5281107Doxercalciferol収率 33.1%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

1α,3β-Diacetoxy-ergosta-5,7,22-trien (X) (200 mg) from Example 7 was dissolved in ether (400 ml) and the solution was irradiated with high pressure mercury lamp (UM-452, Ushio Electric Co., Ltd.) for 10 minutes. After distilling off ether under reduced pressure, ethanol (50 ml) was added and the mixture was heated under reflux for 1 hr. Subsequently, a solution of potassium hydroxide (1 g) in ethanol (10 ml) was added and further heated under reflux for 10 minutes. The whole reaction was carried out in a nitrogen stream. After cooling, the reaction product was extracted with ether (200 ml). The extract was washed with water, dried over Na2SO4 and ether was distilled off under reduced pressure. Chromatography on silica gel of the residue (eluted with 95/5 chloroform/ethyl acetate) gave 55 mg of a crude 1α-hydroxy vitamin D2 (XI). Crystallization of the crude vitamin from hexane/acetone gave 35 mg (17.5% yield) of a pure 1α-hydroxy vitamin D2 (XI) as crystals, m.p. 146°-147° C., λ max 265 nm (ε=18500, ethanol), [α]D20 +47° (c=0.25, ethanol).

後処理

  1. customthe solution was irradiated with high pressure mercury lamp (UM-452, Ushio Electric Co., Ltd.) for 10 minutes
  2. distillationAfter distilling off ether under reduced pressure, ethanol (50 ml)
  3. additionwas added
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 1 hr
  6. additionSubsequently, a solution of potassium hydroxide (1 g) in ethanol (10 ml) was added
  7. temperaturefurther heated
  8. temperatureunder reflux for 10 minutes
  9. customThe whole reaction
  10. temperatureAfter cooling
  11. extractionthe reaction product was extracted with ether (200 ml)
  12. washThe extract was washed with water
  13. dry with materialdried over Na2SO4 and ether
  14. distillationwas distilled off under reduced pressure
  15. washChromatography on silica gel of the residue (eluted with 95/5 chloroform/ethyl acetate)

出典と根拠

ORDレコード
ord-d86e432eb9cf4cbc873ebcdcfaa4376c
出典データセット
uspto-grants-1988_07
特許番号
US04758383

関連ノート

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