4-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-(((2R,5R,6S)-5-hydroxy-6-isobutyl-5,6-dihydro-2H-pyran-2-yl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one | 1268341-24-7

• 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: 4-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-(((2R,5R,6S)-5-hydroxy-6-isobutyl-5,6-dihydro-2H-pyran-2-yl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
• CAS: 1268341-24-7
• 化学式: C₃₂H₄₈O₆
• 分子量: 528.73
• InChiKey: WOJHFOXAGFUBSQ-ZMNYHHRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  38.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-(((2R,5R,6S)-5-hydroxy-6-isobutyl-5,6-dihydro-2H-pyran-2-yl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one 在 N-甲基吗啉 、 2-硝基苯磺酰肼 、 三乙胺 作用下， 反应 24.0h， 以88%的产率得到3-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-[(2R,5R,6S)-5-hydroxy-6-(2-methylpropyl)oxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
  参考文献：
  名称：

  C5′-Alkyl Substitution Effects on Digitoxigenin α-l-Glycoside Cancer Cytotoxicity

  摘要：

  A highly regio- and stereoselective asymmetric synthesis of various CS'-alkyl side chains of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation with postglycosylated dihydroxylation or diimide reduction. The C5'-methyl group in both alpha-L-rhamnose and cc-L-amicetose digitoxin analogues displayed a steric directed apoptosis induction and tumor growth inhibition against nonsmall cell human lung cancer cells (NCI-H460). The antitumor activity is significantly reduced when the steric hindrance is increased at the C5'-stereocenter.

  DOI：

  10.1021/ml100291n
• 作为产物：
  描述：

  1-呋喃-2-基-3-甲基丁烷-1-酮 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 (1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine-ruthenium(mesitylene) 、 cerium(III) chloride 、 sodium formate 、 sodium acetate 、 十六烷基三甲基溴化铵 、 碳酸氢钠 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 37.0h， 生成 4-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-(((2R,5R,6S)-5-hydroxy-6-isobutyl-5,6-dihydro-2H-pyran-2-yl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
  参考文献：
  名称：

  C5′-Alkyl Substitution Effects on Digitoxigenin α-l-Glycoside Cancer Cytotoxicity

  摘要：

  A highly regio- and stereoselective asymmetric synthesis of various CS'-alkyl side chains of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation with postglycosylated dihydroxylation or diimide reduction. The C5'-methyl group in both alpha-L-rhamnose and cc-L-amicetose digitoxin analogues displayed a steric directed apoptosis induction and tumor growth inhibition against nonsmall cell human lung cancer cells (NCI-H460). The antitumor activity is significantly reduced when the steric hindrance is increased at the C5'-stereocenter.

  DOI：

  10.1021/ml100291n