(4S)-3-[(2S,3R,4S)-3-hydroxy-2,4-dimethylhexanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one | 206651-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-3-[(2S,3R,4S)-3-hydroxy-2,4-dimethylhexanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 206651-86-7
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: GEFILQTWDUCFCL-NNYUYHANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-3-[(2S,3R,4S)-3-hydroxy-2,4-dimethylhexanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 以80%的产率得到(2S,3R,4S)-3-hydroxy-2,4-dimethylhexanoic acid
  参考文献：
  名称：

  Structural Elucidation of Twelve Novel Esters Composed of Five Fatty Acids and Three New Branched Alcohols Together with Four Monoterpenoids from Sancassania shanghaiensis (Acari: Acaridae)

  摘要：

  GC/MS分析在Sancassania shanghaiensis的抱粉腺成分中检测到总共12种新型酯和4种单萜（玫瑰呋喃、（2R,3R）-环氧橙花醇以及α-和β-刺檗二醇）。经过水解后的酸性部分由5种常见脂肪酸（棕榈酸、硬脂酸、油酸、亚油酸和花生酸）组成，而醇性部分则主要由两种成分（带有支链甲基的C6和C8醇）组成，同时含有微量的C9醇。通过比较其3,5-二硝基苯甲酸酯的物理化学数据与选择性合成醇的数据，确认这两种主要醇为新型醇[（S）-2-甲基戊醇和（2S,4S）-2,4-二甲基己醇]。根据结构和生物学上的相似性，C9醇被推测为（2S,4S）-2,4-二甲基庚醇。通过GC鉴定，五种化合物分别为五种脂肪酸的（S）-2-甲基戊酯，另外五种成分同样为（2S,4S）-2,4-二甲基己酯。剩下的两种被推测为（2S,4S）-2,4-二甲基庚酯的硬脂酸酯和亚油酸酯。

  DOI：

  10.1271/bbb.65.919
• 作为产物：
  描述：

  S-(-)-2-甲基-1-丁醇 在 三氟甲磺酸二丁硼 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (4S)-3-[(2S,3R,4S)-3-hydroxy-2,4-dimethylhexanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Total synthesis of callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata

  摘要：

  A first total synthesis of callystatin A (1), a potent cytotoxic polyketide from the marine sponge Callyspongia truncata, has been achieved by use of an E-selective Wittig olefination and asymmetric Evans aldol condensation as the key reactions. Thus, the absolute stereostructure of 1 previously established by us was confirmed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00151-8

文献信息

• Structural Determination of (−)-SCH 64874 and Hirsutellomycin by Semisynthesis
  作者：Hidetoshi Tokuyama、Kaori Yamada、Hideto Fujiwara、Juri Sakata、Kentaro Okano、Malipan Sappan、Masahiko Isaka

  DOI：10.1021/acs.joc.6b02452

  日期：2017.1.6

  relative stereochemistry of the β-keto carboxylic acid chain of the analogous alkaloid hirsutellomycin was determined in a stepwise manner. The C4′–C6′ syn relationships were predicted by comparing the NMR data of the corresponding ester fragments with that of hirsutellomycin. The relative stereochemistry of the whole molecule, including the epimerizable C2′ stereocenter, was determined by introduction

  通过半合成确定C 2对称的表二硫代二酮哌嗪生物碱SCH 64874的结构。通过比较四个可能的非对映异构的β-羟基羧酸片段与SCH 64874的NMR数据，可以确定具有三个手性中心的β-羟基羧酸链的相对立体化学。两种对映体的β-羟基羧酸揭示了SCH 64874的相对立体化学。以逐步方式确定了类似生物碱hirsutellomycin的β-酮羧酸链的相对立体化学。该C4'-C6' SYN通过将相应酯片段的NMR数据与hirsutellomycin的NMR数据进行比较，可以预测二者之间的相关性。整个分子的相对立体化学，包括可差向异构的C2'立体中心，是通过将四个可能的侧链引入双脱硫基二（甲硫基）脱乙酰基花生四烯酸核心来确定的。我们发现，C2'的立体化学与受核心结构影响的热力学稳定形式的立体化学趋同。
• Structural Elucidation of Twelve Novel Esters Composed of Five Fatty Acids and Three New Branched Alcohols Together with Four Monoterpenoids from Sancassania shanghaiensis (Acari: Acaridae)
  作者：Tomoyo SAKATA、Kimiko OKABE、Yasumasa KUWAHARA

  DOI：10.1271/bbb.65.919

  日期：2001.1

  A total of 12 novel esters and four monoterpenoids (rosefuran, (2R,3R)-epoxyneral, and α- and β-acaridials) were detected by GC/MS analyses as the opisthonotal gland components of Sancassania shanghaiensis. The acidic fraction after hydrolysis was composed of five common fatty acids (palmitic, stearic, oleic, linoleic and arachidic acid), while the alcoholic fraction consisted of two major components (C6 and C8 alcohols with branched methyls), together with a trace amount of C9 alcohol. The Two major alcohols were identified as new alcohols [(S)-2-methylpentanol and (2S,4S)-2,4-dimethylhexanol] by comparing the physico-chemical data of their 3,5-dinitrobenzoates with those of regio-selectively synthesized alcohols. The C9 alcohol was suggested as (2S,4S)-2,4-dimethylheptanol, based on a structural and biogenetic analogy to the C6 and C8 alcohols. Five of the compounds were each identified by GC to be (S)-2-methylpentyl esters from five fatty acids, and the other five components likewise as (2S,4S)-2,4-dimethylhexyl esters. The remaining two were suggested as (2S,4S)-2,4-dimethylheptyl Stearate and linolate.

  GC/MS分析在Sancassania shanghaiensis的抱粉腺成分中检测到总共12种新型酯和4种单萜（玫瑰呋喃、（2R,3R）-环氧橙花醇以及α-和β-刺檗二醇）。经过水解后的酸性部分由5种常见脂肪酸（棕榈酸、硬脂酸、油酸、亚油酸和花生酸）组成，而醇性部分则主要由两种成分（带有支链甲基的C6和C8醇）组成，同时含有微量的C9醇。通过比较其3,5-二硝基苯甲酸酯的物理化学数据与选择性合成醇的数据，确认这两种主要醇为新型醇[（S）-2-甲基戊醇和（2S,4S）-2,4-二甲基己醇]。根据结构和生物学上的相似性，C9醇被推测为（2S,4S）-2,4-二甲基庚醇。通过GC鉴定，五种化合物分别为五种脂肪酸的（S）-2-甲基戊酯，另外五种成分同样为（2S,4S）-2,4-二甲基己酯。剩下的两种被推测为（2S,4S）-2,4-二甲基庚酯的硬脂酸酯和亚油酸酯。
• Total synthesis of callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata
  作者：Nobutoshi Murakami、Weiqi Wang、Masashi Aoki、Yasuhiro Tsutsui、Masanori Sugimoto、Motomasa Kobayashi

  DOI：10.1016/s0040-4039(98)00151-8

  日期：1998.4

  A first total synthesis of callystatin A (1), a potent cytotoxic polyketide from the marine sponge Callyspongia truncata, has been achieved by use of an E-selective Wittig olefination and asymmetric Evans aldol condensation as the key reactions. Thus, the absolute stereostructure of 1 previously established by us was confirmed. (C) 1998 Elsevier Science Ltd. All rights reserved.