(1S,2R,5R,6R,8R,10S,11S,14S,16S)-5-[(2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-6-methylheptan-2-yl]-14-(methoxymethoxy)-6,11-dimethyl-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 | 316181-12-1

• 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: (1S,2R,5R,6R,8R,10S,11S,14S,16S)-5-[(2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-6-methylheptan-2-yl]-14-(methoxymethoxy)-6,11-dimethyl-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
• CAS: 316181-12-1
• 化学式: C₄₃H₆₅N₃O₆Si
• 分子量: 748.091
• InChiKey: MCLACKYMIRKCPB-WGWAASNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.99
• 重原子数：
  53
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  84.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R,6R,8R,10S,11S,14S,16S)-5-[(2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-6-methylheptan-2-yl]-14-(methoxymethoxy)-6,11-dimethyl-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 吡啶 、 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 三甲基溴硅烷 、 dimethyl sulfide borane 、 氯化二乙基铝 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 4-deacetoxyagosterol A
  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,9R,10R,13S,15S)-5-[(2S,3S)-3-hydroxy-6-methylheptan-2-yl]-13-(methoxymethoxy)-6,10-dimethyl-16,25-diazaheptacyclo[13.10.2.01,9.02,6.010,15.016,25.018,23]heptacosa-18,20,22,26-tetraene-17,24-dione 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 diamide 、 mercury(II) diacetate 、 溶剂黄146 、 间氯过氧苯甲酸 、 三甲基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,2R,5R,6R,8R,10S,11S,14S,16S)-5-[(2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-6-methylheptan-2-yl]-14-(methoxymethoxy)-6,11-dimethyl-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
  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.
• Synthesis and evaluation of 4-deacetoxyagosterol A as an MDR-modulator
  作者：Nobutoshi Murakami、Masanori Sugimoto、Mari Morita、Shin-ichi Akiyama、Motomasa Kobayashi

  DOI：10.1016/s0960-894x(00)00502-3

  日期：2000.11

  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.