(3S,5S,6R,8R,9S,10R,13S,14S,15R,17R)-3,6-Bis-benzyloxy-15-hydroxy-17-((1R,5R)-6-hydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-16-one | 210687-21-1

• 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: (3S,5S,6R,8R,9S,10R,13S,14S,15R,17R)-3,6-Bis-benzyloxy-15-hydroxy-17-((1R,5R)-6-hydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-16-one
• 英文别名: (3S,5S,6R,8R,9S,10R,13S,14S,15R,17R)-15-hydroxy-17-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-3,6-bis(phenylmethoxy)-1,2,3,4,5,6,7,8,9,11,12,14,15,17-tetradecahydrocyclopenta[a]phenanthren-16-one
• CAS: 210687-21-1
• 化学式: C₄₁H₅₈O₅
• 分子量: 630.909
• InChiKey: XAKFWAGULGYDLT-CXLHAAJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,5S,6R,8R,9S,10R,13S,14S,15R,17R)-3,6-Bis-benzyloxy-15-hydroxy-17-((1R,5R)-6-hydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-16-one 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以58%的产率得到(3S,5S,6R,8R,9S,10R,13R,14S,15R,16R,17R)-3,6-Bis-benzyloxy-17-((1R,5R)-6-hydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-15,16-diol
  参考文献：
  名称：

  Synthesis of (25R)-5α-Cholestane-3β,6β,15α,16β,26-pentol, a Cytostatic Starfish Steroid

  摘要：

  The synthesis of (25R)-5 alpha-cholestane-3 beta,6 beta, 15 alpha,16 beta,26-pentol (1a), a marine cytostatic steroid, has been achieved in 13 steps (7.8% overall yield) starting from commercially available diosgenin (2). A key step in the synthesis was the dimethyldioxirane oxidation of the enolsilane 16 to introduce the 15 alpha-hydroxy group in the D ring.

  DOI：

  10.1021/jo980266c
• 作为产物：
  描述：

  薯蓣皂素 在 盐酸 、 sodium hydroxide 、 amalgamated zinc 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 dimethyl sulfide borane 、 camphor-10-sulfonic acid 、 双氧水 、 二甲基二环氧乙烷 、 四丁基碘化铵 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 77.4h， 生成 (3S,5S,6R,8R,9S,10R,13S,14S,15R,17R)-3,6-Bis-benzyloxy-15-hydroxy-17-((1R,5R)-6-hydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-16-one
  参考文献：
  名称：

  Synthesis of (25R)-5α-Cholestane-3β,6β,15α,16β,26-pentol, a Cytostatic Starfish Steroid

  摘要：

  The synthesis of (25R)-5 alpha-cholestane-3 beta,6 beta, 15 alpha,16 beta,26-pentol (1a), a marine cytostatic steroid, has been achieved in 13 steps (7.8% overall yield) starting from commercially available diosgenin (2). A key step in the synthesis was the dimethyldioxirane oxidation of the enolsilane 16 to introduce the 15 alpha-hydroxy group in the D ring.

  DOI：

  10.1021/jo980266c