(R)-1,2,4-butanetriol tribenzoate

• 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: (R)-1,2,4-butanetriol tribenzoate
• 英文别名: (2R)-1,2,4-tris(benzoyloxy)butane；[(3R)-3,4-dibenzoyloxybutyl] benzoate
• 化学式: C₂₅H₂₂O₆
• 分子量: 418.446
• InChiKey: JRRBIPJIOMRZTN-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2E,4Z,6Z,8R)-8,10-bis(benzoyloxy)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-decatriene 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 氧气 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 (R)-1,2,4-butanetriol tribenzoate
  参考文献：
  名称：

  Determination of the Relative and Absolute Stereochemistry of Fostriecin (CI-920)

  摘要：

  The absolute stereochemistry of fostriecin (1, CI-920), a potent antitumor antibiotic presently in Phase I clinical trials at NCI, was determined to be 5R,8R,9R,11R. 2D H-1-H-1 NMR. NOE experiments conducted on the cyclic phosphate derivative 2 and acetonide revealed a syn-diol stereochemical relationship between C8 and C9 and an anti-diol stereochemical relationship between C9 and C11, respectively. The 5R absolute configuration assignment was confirmed by synthesis of the degradation product 8 previously disclosed. Additional degradation studies of 1 to provide 7 and chiral-phase HPLC comparison with a sample of known chirality established the absolute stereochemistry of C11 to be R. This, along with the relative stereochemical assignments established the full set of absolute stereochemistry assignments for 1.

  DOI：

  10.1021/jo962166h

文献信息

• Absolute Configuration of Aflastatin A, a Specific Inhibitor of Aflatoxin Production by <i>Aspergillus </i><i>p</i><i>arasiticus</i>
  作者：Hiroyuki Ikeda、Nobuaki Matsumori、Makoto Ono、Akinori Suzuki、Akira Isogai、Hiromichi Nagasawa、Shohei Sakuda

  DOI：10.1021/jo991284c

  日期：2000.1.1

  Aflastatin A (1) is a specific inhibitor of aflatoxin production by Aspergillus parasiticus. It has the novel structure of a tetramic acid derivative with a long alkyl side chain. The absolute configurations of 29 chiral centers contained in 1 were chemically elucidated in this study. First, four small fragment molecules were prepared from 1 or its methyl ether (2), and their absolute structures were

  Aflastatin A（1）是一种由寄生曲霉产生的黄曲霉毒素的特异性抑制剂。它具有带有长烷基侧链的四酸衍生物的新型结构。在这项研究中化学阐明了1个化合物中29个手性中心的绝对构型。首先，从1或其甲基醚（2）制备四个小片段分子，并将它们的绝对结构分配为N-甲基-D-丙氨酸，（2S，4R）-2、4-二甲基-1,6-己二醇二苯甲酸酯，（R）-3-羟基十二烷酸和（R）-1,1,2,4-丁三醇三苯甲酸酯。接下来，通过NaIO（4）氧化从1中获得具有13个手性中心的无环片段分子3，并通过基于J的构型分析阐明了其相对立体化学。通过分析（3）J（H，H）和（2,3）J（C，H）的耦合常数以及ROE数据，验证了3的相对构型。最后，通过进一步的基于J的构型分析，使用由2个具有28个手性碳的片段分子7，澄清了1个烷基侧链中的所有相对构型。通过将这些相对构型与前四个片段分子的绝对构型联系起来，可以完全确定1的绝对立体化学。
• Determination of the Relative and Absolute Stereochemistry of Fostriecin (CI-920)
  作者：Dale L. Boger、Masataka Hikota、Bryan M. Lewis

  DOI：10.1021/jo962166h

  日期：1997.3.1

  The absolute stereochemistry of fostriecin (1, CI-920), a potent antitumor antibiotic presently in Phase I clinical trials at NCI, was determined to be 5R,8R,9R,11R. 2D H-1-H-1 NMR. NOE experiments conducted on the cyclic phosphate derivative 2 and acetonide revealed a syn-diol stereochemical relationship between C8 and C9 and an anti-diol stereochemical relationship between C9 and C11, respectively. The 5R absolute configuration assignment was confirmed by synthesis of the degradation product 8 previously disclosed. Additional degradation studies of 1 to provide 7 and chiral-phase HPLC comparison with a sample of known chirality established the absolute stereochemistry of C11 to be R. This, along with the relative stereochemical assignments established the full set of absolute stereochemistry assignments for 1.