4-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-(((2R,5R,6S)-5-hydroxy-6-propyl-5,6-dihydro-2H-pyran-2-yl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one | 1268341-22-5

• 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-propyl-5,6-dihydro-2H-pyran-2-yl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
• CAS: 1268341-22-5
• 化学式: C₃₁H₄₆O₆
• 分子量: 514.703
• InChiKey: GWKDVLULRHDAIR-DRHRRTQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  37.0
• 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-propyl-5,6-dihydro-2H-pyran-2-yl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 以74%的产率得到3-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-propyloxan-2-yl]oxy-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：

  (2S,6R)-6-(((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-2-propyl-2H-pyran-3(6H)-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 以83%的产率得到4-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-(((2R,5R,6S)-5-hydroxy-6-propyl-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