(3S)-3-hydroxy-2,2-dimethyloctanoic acid

• 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: (3S)-3-hydroxy-2,2-dimethyloctanoic acid
• 英文别名: (S)-2,2-Dimethyl-3-hydroxyoctanoic acid；S-2,2-dimethyl-3-hydroxyoctanoic acid；2,2-dimethyl-3-hydroxyoctanoic acid；(S)-Dhoa；S-Dhoaa
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: DTXWPIYXTLXYDT-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,5-戊二醇 在 palladium on activated charcoal 2,6-二甲基吡啶 、 sodium hydroxide 、 草酰氯 、 氢气 、 sodium hydride 、 potassium carbonate 、 二甲基亚砜 、 三氟乙酸 、 (4R)-4-iPr-3-[(p-tolyl)sulfonyl]-1,3,2-oxazaborolidin-5-one 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 10.67h， 生成 (3S)-3-hydroxy-2,2-dimethyloctanoic acid
  参考文献：
  名称：

  The Total Synthesis and Stereochemical Revision of Yanucamide A

  摘要：

  GraphicsThe first total synthesis of yanucamide A is reported via amide and ester couplings of the key components. This synthesis has established the configuration at the previously ambiguous 3-position, and also revised the stereochemistry at the 22-position, to give 3S, 12S, 17S, 22S for the natural product.

  DOI：

  10.1021/ol034803d

文献信息

• Dudawalamides A–D, Antiparasitic Cyclic Depsipeptides from the Marine Cyanobacterium <i>Moorea producens</i>
  作者：Jehad Almaliti、Karla L. Malloy、Evgenia Glukhov、Carmenza Spadafora、Marcelino Gutiérrez、William H. Gerwick

  DOI：10.1021/acs.jnatprod.7b00034

  日期：2017.6.23

  A family of 2,2-dimethyl-3-hydroxy-7-octynoic acid (Dhoya)-containing cyclic depsipeptides, named dudawalamides A–D (1–4), was isolated from a Papua New Guinean field collection of the cyanobacterium Moorea producens using bioassay-guided and spectroscopic approaches. The planar structures of dudawalamides A–D were determined by a combination of 1D and 2D NMR experiments and MS analysis, whereas the

  的2,2-二甲基-3-羟基-7-辛炔酸（Dhoya）含环状缩肽，命名为dudawalamides A-d（A家族1 - 4），从蓝藻的巴布亚新几内亚字段集合分离莫雷阿岛producens使用生物测定指导和光谱学方法。杜达拉瓦胺A–D的平面结构是通过1D和2D NMR实验和MS分析的组合确定的，而绝对构型则是通过X射线晶体学，改进的Marfey分析，手性相GCMS和手性相HPLC确定的。Dudawalamides A–D具有广泛的抗寄生虫活性，对哺乳动物细胞的细胞毒性极小。对含Dhoya的脂肽类的比较分析显示，这些NRPS-PKS衍生的代谢物及其衍生物具有令人感兴趣的结构-活性关系特征。
• Expedient synthesis of α,α-dimethyl-β-hydroxy carbonyl scaffolds via Evans’ aldol reaction with a tertiary enolate
  作者：Joshawna K. Nunnery、Takashi L. Suyama、Roger G. Linington、William H. Gerwick

  DOI：10.1016/j.tetlet.2011.03.126

  日期：2011.6

  (DHOYA) and several variants, which are increasingly common fragments encountered in bioactive marine cyanobacterial metabolites, was developed. These fragments were obtained in three steps via a tertiary aldol reaction utilizing an Evans’ chiral auxiliary to afford the desired stereochemistry at the β-hydroxy carbon. Thus far, this methodology has been successfully applied in determination of the absolute

  开发了 3-羟基-2,2-二甲基辛酸 (DHOYA) 和几种变体的有效合成方法，这些变体是生物活性海洋蓝藻代谢物中越来越常见的片段。这些片段是通过叔醛醇反应分三步获得的，该反应利用埃文斯手性助剂在 β-羟基碳上提供所需的立体化学。迄今为止，该方法已成功应用于测定八种蓝藻天然产物的绝对立体化学，包括 VGSC 活化剂 palymramide A。
• Pitipeptolides A and B, New Cyclodepsipeptides from the Marine Cyanobacterium <i>Lyngbya majuscula</i>
  作者：Hendrik Luesch、Ronald Pangilinan、Wesley Y. Yoshida、Richard E. Moore、Valerie J. Paul

  DOI：10.1021/np000456u

  日期：2001.3.1

  Two new cyclodepsipeptides have been isolated from a population of the marine cyanobacterium Lyngbya majuscula collected at Piti Bomb Holes, Guam. They appear to be unique to this particular Guamanian collection and have been named pitipeptolides A (1) and B (2). Their structures have been elucidated by spectroscopic techniques and by characterization of degradation products. Distinctive features include

  从关岛的Piti Bomb Holes收集的海洋蓝藻Lyngbya majuscula种群中分离出了两个新的环二肽。它们似乎是该特定瓜马尼亚收藏中唯一的，并被命名为pitipeptolides A（1）和B（2）。通过光谱技术和降解产物的特征已经阐明了它们的结构。显着特征包括1中存在2,2-二甲基-3-羟基-7-辛酸残基，2中存在2,2-二甲基-3-羟基-7-辛酸残基，先前已证明是生物合成标记蓝细菌代谢产物。吡替肽A（1）和B（2）对LoVo癌细胞显示弱的细胞毒性，但具有中等的抗分枝杆菌活性并刺激弹性蛋白酶活性。
• Kohamamides A, B, and C, Cyclic Depsipeptides from an <i>Okeania</i> sp. Marine Cyanobacterium
  作者：Arihiro Iwasaki、Ikuma Shiota、Shimpei Sumimoto、Teruhiko Matsubara、Toshinori Sato、Kiyotake Suenaga

  DOI：10.1021/acs.jnatprod.7b00256

  日期：2017.6.23

  Kohamamides A, B, and C (1–3), new cyclic depsipeptides that belong to the kulolide superfamily, were isolated from an Okeania sp. marine cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Kohamamide B (2) exhibited moderate cytotoxicity against HL60 cells. Although many natural products in the kulolide superfamily have been isolated from cyanobacteria collected

  Kohamamides A，B，和C（1 - 3），属于该超家族kulolide新的循环缩肽，从一个分离Okeania藻。海洋蓝细菌。通过光谱分析和降解反应阐明了它们的结构。Kohamamide B（2）对HL60细胞表现出中等的细胞毒性。虽然许多天然产品在kulolide超家族已经从世界各地收集蓝藻分离，kohamamides 1 - 3要从东亚海洋环境中分离的首批成员。此外，与该超家族的其他成员不同，Kohamamides 1 – 3 含有与Pro残基相邻的Leu残基，而不是另一个亲脂氨基酸。
• The Total Synthesis and Stereochemical Revision of Yanucamide A
  作者：Zhengshuang Xu、Yungui Peng、Tao Ye

  DOI：10.1021/ol034803d

  日期：2003.8.1

  GraphicsThe first total synthesis of yanucamide A is reported via amide and ester couplings of the key components. This synthesis has established the configuration at the previously ambiguous 3-position, and also revised the stereochemistry at the 22-position, to give 3S, 12S, 17S, 22S for the natural product.