[tert-butyl(dimethyl)silyl] (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate | 146651-13-0

• 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: [tert-butyl(dimethyl)silyl] (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 146651-13-0
• 化学式: C₃₆H₆₈O₃Si₂
• 分子量: 605.105
• InChiKey: PQMUAZQVQYBJHL-RJMRBEJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.0
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [tert-butyl(dimethyl)silyl] (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 生成 (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
  参考文献：
  名称：

  Free radical macrocyclizations from steroid-derived precursors

  摘要：

  Stereoselective free radical addition reactions were studied using steroid-derived templates in an attempt to control product dispersity. Templates were prepared from bifunctional steroids appropriately substituted with initiating and terminating functionality. Free radical initiation in the presence of a polymerizable olefin resulted in the formation of macrocycles that had incorporated monomer. The yield of macrocycle formed was as high as 51 % for templates derived from lithocholic acid whereas templates derived from androstanolone failed to give significant amounts of macrocycles. The effects of variation of initiating and terminating functionality, steroid, and olefin on macrocycle size and yield were examined.

  DOI：

  10.1021/jo00057a034
• 作为产物：
  描述：

  石胆酸 、 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 4.0h， 以17.7 g的产率得到[tert-butyl(dimethyl)silyl] (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
  参考文献：
  名称：

  Free radical macrocyclizations from steroid-derived precursors

  摘要：

  Stereoselective free radical addition reactions were studied using steroid-derived templates in an attempt to control product dispersity. Templates were prepared from bifunctional steroids appropriately substituted with initiating and terminating functionality. Free radical initiation in the presence of a polymerizable olefin resulted in the formation of macrocycles that had incorporated monomer. The yield of macrocycle formed was as high as 51 % for templates derived from lithocholic acid whereas templates derived from androstanolone failed to give significant amounts of macrocycles. The effects of variation of initiating and terminating functionality, steroid, and olefin on macrocycle size and yield were examined.

  DOI：

  10.1021/jo00057a034

文献信息

• Free radical macrocyclizations from steroid-derived precursors
  作者：Daniel M. Scott、Andrew T. McPhail、Ned A. Porter

  DOI：10.1021/jo00057a034

  日期：1993.2

  Stereoselective free radical addition reactions were studied using steroid-derived templates in an attempt to control product dispersity. Templates were prepared from bifunctional steroids appropriately substituted with initiating and terminating functionality. Free radical initiation in the presence of a polymerizable olefin resulted in the formation of macrocycles that had incorporated monomer. The yield of macrocycle formed was as high as 51 % for templates derived from lithocholic acid whereas templates derived from androstanolone failed to give significant amounts of macrocycles. The effects of variation of initiating and terminating functionality, steroid, and olefin on macrocycle size and yield were examined.