(3S,4S,5S,10S,13R,17R)-17-((1R,3S)-3-Hydroxy-1,5-dimethyl-hexyl)-4,10,13-trimethyl-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol | 119760-84-8

• 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,4S,5S,10S,13R,17R)-17-((1R,3S)-3-Hydroxy-1,5-dimethyl-hexyl)-4,10,13-trimethyl-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 英文别名: (3S,4S,5S,10S,13R,17R)-17-[(2R,4S)-4-hydroxy-6-methylheptan-2-yl]-4,10,13-trimethyl-2,3,4,5,6,7,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 119760-84-8
• 化学式: C₂₈H₄₆O₂
• 分子量: 414.672
• InChiKey: DRLJEKZHMXXVBZ-XGDUKEAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4S,5S,10S,13R,17R)-17-((1R,3S)-3-Hydroxy-1,5-dimethyl-hexyl)-4,10,13-trimethyl-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol 、 甲氧基-三氟甲基苯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以5.2 mg的产率得到[(3S,4S,5S,10S,13R,17R)-4,10,13-trimethyl-17-[(2R,4S)-6-methyl-4-[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxyheptan-2-yl]-2,3,4,5,6,7,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Bioactive steroidal glycosides from the marine sponge Erylus lendenfeldi

  摘要：

  Bioassay-guided fractionation of the methanol extract of Erylus lendenfeldi using engineered strains of budding yeast (Saccharomyces cerevisiae) has resulted in the isolation of the known compound eryloside A (1) and two new compounds, erylosides K (2) and L (3). The structures were established based mainly on 1D and 2D NMR data. The absolute stereochemistry of eryloside A, which had never been fully characterized, was determined using the modified Mosher's method. The absolute stereochemistry of eryloside K was determined by comparison with tetrahydroeryloside A. Compounds 1-3 exhibited selective cytotoxicity against a yeast strain (Deltarad50) deficient in double strand break (DSB) repair. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.039
• 作为产物：
  描述：

  eryloside A 在 盐酸 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.0h， 生成 (3S,4S,5S,10S,13R,17R)-17-((1R,3S)-3-Hydroxy-1,5-dimethyl-hexyl)-4,10,13-trimethyl-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
  参考文献：
  名称：

  Bioactive steroidal glycosides from the marine sponge Erylus lendenfeldi

  摘要：

  Bioassay-guided fractionation of the methanol extract of Erylus lendenfeldi using engineered strains of budding yeast (Saccharomyces cerevisiae) has resulted in the isolation of the known compound eryloside A (1) and two new compounds, erylosides K (2) and L (3). The structures were established based mainly on 1D and 2D NMR data. The absolute stereochemistry of eryloside A, which had never been fully characterized, was determined using the modified Mosher's method. The absolute stereochemistry of eryloside K was determined by comparison with tetrahydroeryloside A. Compounds 1-3 exhibited selective cytotoxicity against a yeast strain (Deltarad50) deficient in double strand break (DSB) repair. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.039