(20S)-3β,23-dihydroxy-24-nor-17-azachol-5-en-16-one 3-tert-butyl-dimethylsilyl ether | 164800-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉类
• 英文名称: (20S)-3β,23-dihydroxy-24-nor-17-azachol-5-en-16-one 3-tert-butyl-dimethylsilyl ether
• CAS: 164800-23-1
• 化学式: C₂₈H₄₉NO₃Si
• 分子量: 475.787
• InChiKey: XMASJJGADLDJKS-OKOOHBEHSA-N

物化性质

• 熔点：
  179-182 °C(Solvent: Dichloromethane; Hexane)
• 沸点：
  559.3±50.0 °C(predicted)
• 密度：
  1.05±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  (20S)-3β,23-dihydroxy-24-nor-17-azachol-5-en-16-one 3-tert-butyl-dimethylsilyl ether 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (20S)-3β-hydroxy-16-oxo-24-nor-17-azachol-5-enaldehyde tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Morzycki, Jacek W.; Lotowski, Zenon, Heterocycles, 1995, vol. 41, # 5, p. 931 - 936

  摘要：

  DOI：
• 作为产物：
  描述：

  3-[(3S,8R,9S,10R,13S,14S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-16-oxo-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17-aza-cyclopenta[a]phenanthren-17-yl]-butyric acid methyl ester 在 lithium aluminium tetrahydride 、 乙酸乙酯 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 (20R)-3β,23-dihydroxy-24-nor-17-azachol-5-en-16-one 3-tert-butyl-dimethylsilyl ether 、 (20S)-3β,23-dihydroxy-24-nor-17-azachol-5-en-16-one 3-tert-butyl-dimethylsilyl ether
  参考文献：
  名称：

  Studies on the construction of the 2-isooctyl side chain in 17-azasteroids

  摘要：

  The transformations of (20R)- and (20S)-3 beta-hydroxy-16-oxo-24-nor-17-azachol-5-eno-23-nitriles towards the 17-aza analogue of cholesterol are described. Attempts of a direct addition of a four carbon atom fragment to nitriles were unsuccessful. Alternately, nitriles were transformed via carboxylic acids, methyl esters and primary alcohols into iodides. The coupling reaction of(20S)-iodide with (i-Bu)(2)CuLi afforded the desired product in low yield but failed in the case of the 20R epimer.

  DOI：

  10.1007/bf00811765