(5α,7α,24S)-24-hydroxy-7-(methoxymethoxy)cholestan-3-one | 952312-06-0

• 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: (5α,7α,24S)-24-hydroxy-7-(methoxymethoxy)cholestan-3-one
• 英文别名: (5S,7R,8R,9S,10S,13R,14S,17R)-17-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-7-(methoxymethoxy)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 952312-06-0
• 化学式: C₂₉H₅₀O₄
• 分子量: 462.714
• InChiKey: IPMXJHLRPUOBPX-NGZWQPFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5α,7α,24S)-24-hydroxy-7-(methoxymethoxy)cholestan-3-one 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 pyridine-SO3 complex 、 3 A molecular sieve 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-[3-[[(3β,5α,7α,24S)-7,24-bis(sulfooxy)cholestan-3-yl]amino]propyl]-2-pyrrolidinone disodium salt
  参考文献：
  名称：

  Details of the Structure Determination of the Sulfated Steroids PSDS and PADS:  New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone

  摘要：

  [GRAPHICS]The discovery of two new components of the migratory pheromone used by sea lamprey to guide adults to spawning grounds was recently reported. These hold promise for use in a pheromone-based control program for this species, an invasive pest in the Great Lakes. Details of the structure determination of these steroidal bis-sulfates [petromyzosterol disulfate (PSDS, 2) and petromyzonamine disulfate (PADS, 3)] are described here. Pattern matching of H-1 NMR data was particularly valuable. This involved comparison of spectra of the natural samples of 2 and 3 with those of appropriate steroidal analogues [e.g., petromyzonol sulfate (PS, 1, a previously known sea lamprey bile acid derivative that is a third component of the migratory pheromone), cholesterol sulfate (6), and squalamine (8)] and model compounds containing the unprecedented aminolactam substructure present in 3. The logic underlying the iterative analyses used is presented.

  DOI：

  10.1021/jo070957l
• 作为产物：
  描述：

  异丙基氯化镁 、 (R)-4-((5S,7R,8R,9S,10S,13R,14S,17R)-7-Methoxymethoxy-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanal 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 (5α,7α,24S)-24-hydroxy-7-(methoxymethoxy)cholestan-3-one 、 (5α,7α,24R)-24-hydroxy-7-(methoxymethoxy)cholestan-3-one
  参考文献：
  名称：

  Details of the Structure Determination of the Sulfated Steroids PSDS and PADS:  New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone

  摘要：

  [GRAPHICS]The discovery of two new components of the migratory pheromone used by sea lamprey to guide adults to spawning grounds was recently reported. These hold promise for use in a pheromone-based control program for this species, an invasive pest in the Great Lakes. Details of the structure determination of these steroidal bis-sulfates [petromyzosterol disulfate (PSDS, 2) and petromyzonamine disulfate (PADS, 3)] are described here. Pattern matching of H-1 NMR data was particularly valuable. This involved comparison of spectra of the natural samples of 2 and 3 with those of appropriate steroidal analogues [e.g., petromyzonol sulfate (PS, 1, a previously known sea lamprey bile acid derivative that is a third component of the migratory pheromone), cholesterol sulfate (6), and squalamine (8)] and model compounds containing the unprecedented aminolactam substructure present in 3. The logic underlying the iterative analyses used is presented.

  DOI：

  10.1021/jo070957l

文献信息

• Details of the Structure Determination of the Sulfated Steroids PSDS and PADS:  New Components of the Sea Lamprey (<i>Petromyzon </i><i>marinus</i>) Migratory Pheromone
  作者：Thomas R. Hoye、Vadims Dvornikovs、Jared M. Fine、Kari R. Anderson、Christopher S. Jeffrey、David C. Muddiman、Feng Shao、Peter W. Sorensen、Jizhou Wang

  DOI：10.1021/jo070957l

  日期：2007.9.1

  [GRAPHICS]The discovery of two new components of the migratory pheromone used by sea lamprey to guide adults to spawning grounds was recently reported. These hold promise for use in a pheromone-based control program for this species, an invasive pest in the Great Lakes. Details of the structure determination of these steroidal bis-sulfates [petromyzosterol disulfate (PSDS, 2) and petromyzonamine disulfate (PADS, 3)] are described here. Pattern matching of H-1 NMR data was particularly valuable. This involved comparison of spectra of the natural samples of 2 and 3 with those of appropriate steroidal analogues [e.g., petromyzonol sulfate (PS, 1, a previously known sea lamprey bile acid derivative that is a third component of the migratory pheromone), cholesterol sulfate (6), and squalamine (8)] and model compounds containing the unprecedented aminolactam substructure present in 3. The logic underlying the iterative analyses used is presented.