(2R,3S)-3-hydroxy-2-methylnonanoic acid | 247579-05-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2R,3S)-3-hydroxy-2-methylnonanoic acid
• CAS: 247579-05-1
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: NEZKGLDQZZMTBH-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  13.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-hydroxy-2-methylnonanoic acid 在 四(三苯基膦)钯 吗啉 、 4-二甲氨基吡啶 、 氰基磷酸二乙酯 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 67.0h， 生成 4-epi-24-O-benzyl-globomycin
  参考文献：
  名称：

  Structure–activity relationships of globomycin analogues as antibiotics

  摘要：

  Globomycin (1a), a signal peptidase II inhibitor, and its derivatives show potent antibacterial activity against Gram-negative bacteria. The synthesis and antimicrobial activity of novel globomycin analogues are reported. The hydroxyl group in the L-Ser residue was essential for the antimicrobial activity and the length of the alkyl side chain greatly influenced the activity. In addition, derivatives that had a modified cyclic core exhibited weak activity. One of the analogues showed a wider antimicrobial spectrum, effective against not only Gram-negative but also Gram-positive bacteria. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.055
• 作为产物：
  描述：

  (4R,5S)-3-[(2R,3S)-(3-hydroxy-2-methylnonanoyl)]-4-methyl-5-phenyloxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 水 为溶剂， 以100%的产率得到(2R,3S)-3-hydroxy-2-methylnonanoic acid
  参考文献：
  名称：

  Structure–activity relationships of globomycin analogues as antibiotics

  摘要：

  Globomycin (1a), a signal peptidase II inhibitor, and its derivatives show potent antibacterial activity against Gram-negative bacteria. The synthesis and antimicrobial activity of novel globomycin analogues are reported. The hydroxyl group in the L-Ser residue was essential for the antimicrobial activity and the length of the alkyl side chain greatly influenced the activity. In addition, derivatives that had a modified cyclic core exhibited weak activity. One of the analogues showed a wider antimicrobial spectrum, effective against not only Gram-negative but also Gram-positive bacteria. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.055

文献信息

• Synthesis, Equilibration, and Coupling of 4-Lithio-1,3-dioxanes:  Synthons for <i>syn</i>- and <i>a</i><i>nti</i>-1,3-Diols
  作者：Scott D. Rychnovsky、Alexandre J. Buckmelter、Vilas H. Dahanukar、Donald J. Skalitzky

  DOI：10.1021/jo9909352

  日期：1999.9.1

  inefficient equilibration with this hindered substrate is attributed to a slow rate of equilibration rather than insufficient driving force. These alkyllithium reagents could be coupled with a variety of electrophiles with retention of configuration by direct addition, copper-mediated coupling, or transmetalation to the corresponding alkylzinc reagent followed by copper-mediated coupling.

  通过对4-（苯硫基）-1,3-二恶烷进行还原锂化来制备构型确定的α-烷氧基锂试剂。在1，3-二恶烷-4-酮的还原和原位乙酰化的基础上，已经开发了4-（苯硫基）-1，3-二恶烷的新的和更通用的合成方法。对于所检查的每种取代模式（23a-d），还原锂化作用均产生具有99：1立体选择性的轴向烷基锂（24a-d）。这些烷基锂试剂与不受阻碍的底物的平衡是可能的，以得到具有优异的立体选择性的赤道烷基锂26a和26b。受阻更大的轴向烷基锂试剂（24c，24d）不能有效地平衡。烷基锂试剂24c和26c之间的平衡强烈有利于赤道异构体26c。与该受阻基质的无效平衡归因于平衡速率慢而不是驱动力不足。这些烷基锂试剂可通过直接添加，铜介导的偶联或与相应的烷基锌试剂的重金属化然后铜介导的偶联而与构型保持的亲电试剂偶联。