(25R)-3β-(t-butyldimethylsilyloxy)-5α-spirostane-5,6β-diol | 876908-18-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (25R)-3β-(t-butyldimethylsilyloxy)-5α-spirostane-5,6β-diol
• 英文别名: (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18R,19R)-16-[tert-butyl(dimethyl)silyl]oxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-18,19-diol
• CAS: 876908-18-8
• 化学式: C₃₃H₅₈O₅Si
• 分子量: 562.906
• InChiKey: ZDXZEQHYZAXYJC-YOQGJUTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  39
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (25R)-3β-(t-butyldimethylsilyloxy)-5α-spirostane-5,6β-diol 在 吡啶 、 四丁基氟化铵 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (25R)-3-oxa-6β-acetoxy-5-hydroxy-4a-homo-5α-spirostan-4-one
  参考文献：
  名称：

  Synthesis of peptidomimetic-spirostane hybrids via Ugi reaction: a versatile approach for the formation of peptide–steroid conjugates

  摘要：

  A general approach towards the preparation of peptide-steroid conjugates has been addressed. Utilizing the Ugi reaction, five peptidomimetic-steroid hybrids were achieved in good to excellent yields from carboxy- and amino-spirostanes and mono-protected alpha-amino acids. Diverse synthetic routes, specially focused on the formation of secosteroids, were implemented to introduce Ugi-type functionalities at different positions of the steroidal nucleus. This versatile approach is suitable for the formation of stable conjugates of steroids with other biologically relevant molecules. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.050
• 作为产物：
  描述：

  (25R)-spirostan-22α-O-3β,5α,6β-triol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以84%的产率得到(25R)-3β-(t-butyldimethylsilyloxy)-5α-spirostane-5,6β-diol
  参考文献：
  名称：

  Novel 5β-hydroxyspirostan-6-ones ecdysteroid antagonists: Synthesis and biological testing

  摘要：

  Eight new 5 beta-hydroxy-spirostan-6-ones bearing hydroxy and amino functions in the A ring, i.e., 3 beta-OH, 3 alpha-OH, 2 beta,3 beta-OH, 2 alpha,3 beta-OH, 3 beta-NH2, 2 alpha-NH2-3 beta-OH, 2 beta-NH2-3 beta-OH, and 2 beta-OH-3 beta-NH2, were efficiently synthesized, and their antiecdysteroid activities were evaluated on the metamorphosis bioassay of mosquito Aedes aegypti. To our knowledge, these new steroids represent the first 5 beta-hydroxy-spirostanes which have been tested for antiecdysteroid activity in mosquitoes. The higher antagonistic effect was found for compounds bearing the 3 beta-hydroxy and 2 beta,3 beta-dihydroxy functionality which show promise as environmental friendly insecticides. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.02.024