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

• 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: (3S,5S,6R,8R,9S,10R,13S,14S,17R)-3,6-Bis-benzyloxy-17-[(1R,5R)-6-(tert-butyl-dimethyl-silanyloxy)-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,17R)-17-[(2R,6R)-7-[tert-butyl(dimethyl)silyl]oxy-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: 210687-15-3
• 化学式: C₄₇H₇₂O₄Si
• 分子量: 729.172
• InChiKey: UPNGIXNOUFBAER-LLPLPNBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.07
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,5S,6R,8R,9S,10R,13S,14S,17R)-3,6-Bis-benzyloxy-17-[(1R,5R)-6-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-hexyl]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-16-one 在 四(三苯基膦)钯 、 三正丁基氢锡 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 [(2R,6R)-6-((3S,5S,6R,8R,9S,10R,13R,14S,17S)-3,6-Bis-benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptyloxy]-tert-butyl-dimethyl-silane
  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 、 双氧水 、 四丁基碘化铵 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 60.4h， 生成 (3S,5S,6R,8R,9S,10R,13S,14S,17R)-3,6-Bis-benzyloxy-17-[(1R,5R)-6-(tert-butyl-dimethyl-silanyloxy)-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

文献信息

• Synthesis of (25<i>R</i>)-5α-Cholestane-3β,6β,15α,16β,26-pentol, a Cytostatic Starfish Steroid
  作者：Irene Izzo、Francesco De Riccardis、Guido Sodano

  DOI：10.1021/jo980266c

  日期：1998.6.1

  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.