(3S,9S,10R,11R,13R,14R,17R)-17-((R)-1,5-Dimethyl-hexyl)-3-methoxymethoxy-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-ol | 316181-15-4

• 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,9S,10R,11R,13R,14R,17R)-17-((R)-1,5-Dimethyl-hexyl)-3-methoxymethoxy-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-ol
• 英文别名: (3S,9S,10R,11R,13R,14R,17R)-3-(methoxymethoxy)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-11-ol
• CAS: 316181-15-4
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: WHJIZYBYWPNHNG-UJZFVAGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,9S,10R,11R,13R,14R,17R)-17-((R)-1,5-Dimethyl-hexyl)-3-methoxymethoxy-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-ol 在 吡啶 、 2,6-二甲基吡啶 、 三甲基溴硅烷 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 Acetic acid (3S,5S,6S,9R,10S,11R,13R,14R,17R)-3-acetoxy-11-(tert-butyl-dimethyl-silanyloxy)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl ester
  参考文献：
  名称：

  Synthesis and evaluation of 4-deacetoxyagosterol A as an MDR-modulator

  摘要：

  4-Deacetoxyagosterol A was synthesized from ergosterol by utilizing reductive regioselective epoxy cleavage as a key reaction. This synthesized congener of agosterol A, a spongean MDR-modulator, showed similar MDR-modulating activity against KB CV-60 cells overexpressing MRP. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00502-3
• 作为产物：
  描述：

  (1S,2R,5R,6R,8R,10S,11S,14S,16S)-14-(methoxymethoxy)-6,11-dimethyl-5-[(2R)-6-methylheptan-2-yl]-19-phenyl-9-oxa-17,19,21-triazaheptacyclo[14.5.2.01,10.02,6.08,10.011,16.017,21]tricos-22-ene-18,20-dione 在 lithium aluminium tetrahydride 、 氯化二乙基铝 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(3S,9S,10R,11R,13R,14R,17R)-17-((R)-1,5-Dimethyl-hexyl)-3-methoxymethoxy-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-ol
  参考文献：
  名称：

  Synthesis and evaluation of 4-deacetoxyagosterol A as an MDR-modulator

  摘要：

  4-Deacetoxyagosterol A was synthesized from ergosterol by utilizing reductive regioselective epoxy cleavage as a key reaction. This synthesized congener of agosterol A, a spongean MDR-modulator, showed similar MDR-modulating activity against KB CV-60 cells overexpressing MRP. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00502-3

文献信息

• Total Synthesis of Agosterol A: an MDR-Modulator from a Marine Sponge
  作者：Nobutoshi Murakami、Masanori Sugimoto、Mari Morita、Motomasa Kobayashi

  DOI：10.1002/1521-3765(20010618)7:12<2663::aid-chem26630>3.0.co;2-u

  日期：2001.6.18

  The first total synthesis of agosterol A, a modulator of multidrug resistance (MDR) mediated by P-gp and MRP1, and isolated from a marine sponge, was achieved from ergosterol by utilizing a regioselective epoxy-cleavage reaction and regioselective dehydroxylation as the key reactions.