(3R,4R)-5-(benzyloxy)-4-methylpentane-1,3-diol | 115508-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4R)-5-(benzyloxy)-4-methylpentane-1,3-diol
• 英文别名: (3R,4R)-4-methyl-5-phenylmethoxypentane-1,3-diol
• CAS: 115508-76-4
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: AYELXLZXGROWSI-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-5-(benzyloxy)-4-methylpentane-1,3-diol 在 palladium on activated charcoal 咪唑 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.5h， 生成 (3R,4R)-4,6-di(tert-butyldimethylsilyloxy)-3-methylhexanenitrile
  参考文献：
  名称：

  Stereostructure of a Novel Cytotoxic 18-Membered Macrolactone Antibiotic FD-891

  摘要：

  [GRAPHICS]The absolute stereochemistry of FD-891, a novel cytotoxic 18-membered macrolactone antibiotic, was determined by a synthetic approach as well as X-ray diffraction of degradative derivatives. The absolute configuration of FD-891 turned out to be as shown above. The stable conformer of FD-891 was also discussed with respect to biological activity by comparison with the structurally related concanamycin A on the bases of molecular mechanics calculations.

  DOI：

  10.1021/ol026518k
• 作为产物：
  描述：

  (2E,4S)-5-(benzyloxy)-4-methyl-2-penten-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 红铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (3R,4R)-5-(benzyloxy)-4-methylpentane-1,3-diol
  参考文献：
  名称：

  Vicenistatin（一种新型的20元大环内酰胺类抗肿瘤抗生素）的绝对立体化学

  摘要：

  通过合成方法确定抗肿瘤抗生素维斯他汀（1）的糖苷配基部分的绝对立体化学。通过立体化学确定的化学方法，将从天然1降解的两种相关组分与由已知化合物制备的相应合成标准品进行了比较。的绝对构型1原来是6小号，7小号，18小号。

  DOI：

  10.1016/s0040-4039(98)00454-7

文献信息

• Absolute stereochemistry of vicenistatin, a novel 20-membered macrocyclic lactam antitumor antibiotic
  作者：Hiroko Arai、Yoshitaka Matsushima、Tadashi Eguchi、Kazutoshi Shindo、Katsumi Kakinuma

  DOI：10.1016/s0040-4039(98)00454-7

  日期：1998.5

  The absolute stereochemistry of the aglycon part of an antitumor antibiotic vicenistatin (1) was determined by a synthetic approach. Two relevant components degradatively derived from natural 1 were compared with the corresponding synthetic standards prepared from known compounds by stereochemically defined chemistry. The absolute configuration of 1 turned out to be 6S,7S,18S.

  通过合成方法确定抗肿瘤抗生素维斯他汀（1）的糖苷配基部分的绝对立体化学。通过立体化学确定的化学方法，将从天然1降解的两种相关组分与由已知化合物制备的相应合成标准品进行了比较。的绝对构型1原来是6小号，7小号，18小号。
• Stereostructure of a Novel Cytotoxic 18-Membered Macrolactone Antibiotic FD-891
  作者：Tadashi Eguchi、Kayako Kobayashi、Hidehiro Uekusa、Yuji Ohashi、Kazutoshi Mizoue、Yoshitaka Matsushima、Katsumi Kakinuma

  DOI：10.1021/ol026518k

  日期：2002.10.1

  [GRAPHICS]The absolute stereochemistry of FD-891, a novel cytotoxic 18-membered macrolactone antibiotic, was determined by a synthetic approach as well as X-ray diffraction of degradative derivatives. The absolute configuration of FD-891 turned out to be as shown above. The stable conformer of FD-891 was also discussed with respect to biological activity by comparison with the structurally related concanamycin A on the bases of molecular mechanics calculations.