[(2S,3R,4S,5S)-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-17-[(2S)-1-dodecoxy-1-oxopropan-2-yl]-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxy-4-prop-2-enoxyoxan-3-yl] 4-methoxybenzoate | 931421-40-8

• 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: [(2S,3R,4S,5S)-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-17-[(2S)-1-dodecoxy-1-oxopropan-2-yl]-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxy-4-prop-2-enoxyoxan-3-yl] 4-methoxybenzoate
• CAS: 931421-40-8
• 化学式: C₅₀H₇₆O₁₁
• 分子量: 853.147
• InChiKey: XTZSEISYYVEPDI-ULUQJDEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  61
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,5S)-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-17-[(2S)-1-dodecoxy-1-oxopropan-2-yl]-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxy-4-prop-2-enoxyoxan-3-yl] 4-methoxybenzoate 、 丙烯酸乙酯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到
  参考文献：
  名称：

  Synthesis of OSW saponin analogs with modified sugar residues and their antiproliferative activities

  摘要：

  Eight monosaccharide analogs of the potent antitumor OSW saponins (2-9) were synthesized. One analog, 2-O-acetyl-aL-arabinopyranoside 3, showed antiproliferative activity against the Jurkat cells (IC50 = 0.078 mu M) comparable to that of the disaccharide derivative (1). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.032
• 作为产物：
  描述：

  (S)-2-[(3S,8R,9S,10R,13S,14S,16S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-16,17-dihydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propionic acid dodecyl ester 在 三氟甲磺酸三甲基硅酯 、 氟化氢吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 [(2S,3R,4S,5S)-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-17-[(2S)-1-dodecoxy-1-oxopropan-2-yl]-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxy-4-prop-2-enoxyoxan-3-yl] 4-methoxybenzoate
  参考文献：
  名称：

  Synthesis of OSW saponin analogs with modified sugar residues and their antiproliferative activities

  摘要：

  Eight monosaccharide analogs of the potent antitumor OSW saponins (2-9) were synthesized. One analog, 2-O-acetyl-aL-arabinopyranoside 3, showed antiproliferative activity against the Jurkat cells (IC50 = 0.078 mu M) comparable to that of the disaccharide derivative (1). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.032

文献信息

• Synthesis of OSW saponin analogs with modified sugar residues and their antiproliferative activities
  作者：Pingping Tang、Fatemah Mamdani、Xiaoyi Hu、Jun O. Liu、Biao Yu

  DOI：10.1016/j.bmcl.2006.11.032

  日期：2007.2

  Eight monosaccharide analogs of the potent antitumor OSW saponins (2-9) were synthesized. One analog, 2-O-acetyl-aL-arabinopyranoside 3, showed antiproliferative activity against the Jurkat cells (IC50 = 0.078 mu M) comparable to that of the disaccharide derivative (1). (c) 2006 Elsevier Ltd. All rights reserved.