(3S,9S,10R,11R,13R,14R,17R)-17-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-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 | 316181-14-3

• 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-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-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)-17-[(2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-6-methylheptan-2-yl]-3-(methoxymethoxy)-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-11-ol
• CAS: 316181-14-3
• 化学式: C₃₅H₆₂O₄Si
• 分子量: 574.96
• InChiKey: ABCOVSYCXLPFPO-OSKRHANASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.91
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,9S,10R,11R,13R,14R,17R)-17-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-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 、 dimethyl sulfide borane 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 52.0h， 生成 acetic acid 3,4-diacetoxy-11-(tert-butyl-dimethyl-silanyloxy)-17-[2-(tert-butyl-dimethyl-silanyloxy)-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：

  Total Synthesis of Agosterol A: an MDR-Modulator from a Marine Sponge

  摘要：

  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.

  DOI：

  10.1002/1521-3765(20010618)7:12<2663::aid-chem26630>3.0.co;2-u
• 作为产物：
  描述：

  tert-Butyl-{(R)-1-[(S)-1-((3S,10S,13R,14R,17R)-3-methoxymethoxy-10,13-dimethyl-2,3,4,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl]-4-methyl-pentyloxy}-dimethyl-silane 在 lithium aluminium tetrahydride 、 氯化二乙基铝 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 生成 (3S,9S,10R,11R,13R,14R,17R)-17-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-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