(22S)-3α-t-butyldimethylsilyloxy-22-allyloxy-26,27-dinor-5β-furost-24-en-22-ol | 1207866-70-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (22S)-3α-t-butyldimethylsilyloxy-22-allyloxy-26,27-dinor-5β-furost-24-en-22-ol
• CAS: 1207866-70-3
• 化学式: C₃₄H₅₈O₃Si
• 分子量: 542.918
• InChiKey: DGIKVADEPVIMIW-CXCLTTSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.16
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (22S)-3α-t-butyldimethylsilyloxy-22-allyloxy-26,27-dinor-5β-furost-24-en-22-ol 在 Grubbs catalyst first generation 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以91%的产率得到27-nor-5β-spirost-24-en-3α-ol t-butyldimethylsilyl ether
  参考文献：
  名称：

  Synthesis of “glycospirostanes” via ring-closing metathesis

  摘要：

  Syntheses of "glycospirostanes" from 3 beta-hydroxy-23,24-dinor-5 alpha-cholano-22,16-lactone and 3 alpha-hydroxy-23,24-dinor-5 beta- -cholano-22,16-lactone were performed. The key step of these syntheses was ring-closing metathesis of the corresponding C,O-diallyl derivative. Further elaboration of the six-membered ring F consisted of allylic hydroxylation with SeO(2) followed by OsO(4) dihydroxylation of the C24-C25 double bond. The obtained final products proved to be simultaneously O- and C-L-arabinopyranosides. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.09.001
• 作为产物：
  描述：

  (20S,22S)-3α-t-butyldimethylsilyloxy-26,27-dinor-5β-furost-24-en-22-ol 、 烯丙醇 在 双三氟甲烷磺酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以70%的产率得到(22S)-3α-t-butyldimethylsilyloxy-22-allyloxy-26,27-dinor-5β-furost-24-en-22-ol
  参考文献：
  名称：

  Synthesis of “glycospirostanes” via ring-closing metathesis

  摘要：

  Syntheses of "glycospirostanes" from 3 beta-hydroxy-23,24-dinor-5 alpha-cholano-22,16-lactone and 3 alpha-hydroxy-23,24-dinor-5 beta- -cholano-22,16-lactone were performed. The key step of these syntheses was ring-closing metathesis of the corresponding C,O-diallyl derivative. Further elaboration of the six-membered ring F consisted of allylic hydroxylation with SeO(2) followed by OsO(4) dihydroxylation of the C24-C25 double bond. The obtained final products proved to be simultaneously O- and C-L-arabinopyranosides. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.09.001