(2S)-1,2-O-isopropyliden-octadec-3(Z)-ene-1,2-diol | 111394-70-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-1,2-O-isopropyliden-octadec-3(Z)-ene-1,2-diol
• 英文别名: (4S)-4-[(Z)-hexadec-1-enyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 111394-70-8
• 化学式: C₂₁H₄₀O₂
• 分子量: 324.547
• InChiKey: GUYLYVNKSPTSLO-IVFAQJDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  23.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S)-1,2-O-isopropyliden-octadec-3(Z)-ene-1,2-diol 生成 (1S,2S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]hexadecane-1,2-diol
  参考文献：
  名称：

  KUMAR, VIJAY;DEV, SUKH, TETRAHEDRON, 43,(1987) N 24, 5933-5948

  摘要：

  DOI：
• 作为产物：
  描述：

  溴代十五烷 在 苯基锂 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 18.17h， 生成 (2S)-1,2-O-isopropyliden-octadec-3(Z)-ene-1,2-diol
  参考文献：
  名称：

  阿育吠陀粗药的化学-VII 1琼脂（来自Commiphora Mukul的树脂）-6：琼脂甾醇的绝对立体化学

  摘要：

  以阐明quqqultetrols，皂化的部件的立体化学没药穆库尔树脂，D-来苏- ，L-核糖- ，和L-木糖-octadecane -1,2,3,4-四醇已经通过两种不同的路线合成。一种方法从D-甘油醛开始，而第二种方法则基于适当的戊糖。天然产物guggultetrol-18的绝对构型，已经推导出D-木糖（2小号，3小号，4 - [R通过与合成化合物直接比较-构型）。这项工作还有助于建立古格列特20的手性。

  DOI：

  10.1016/s0040-4020(01)87799-1

文献信息

• Synthesis and Bioassay of Neurogenically Potent Gangliosides DSG-A, Hp-s1 and Their Analogues
  作者：Ganesh B. Shelke、Yu-Hsuan Lih、Ying-Ju Liao、Chih-Wu Liang、Tzer-Min Kuo、Ying-Chin Ko、Shun-Yuan Luo

  DOI：10.1021/acschemneuro.8b00055

  日期：2018.6.20

  the search of a potent candidate for neurotherapy, we designed and synthesized various analogues of ganglioside Hp-s1. The modification includes the change in hydrophobicity by varying the carbon chain length, altering the number of hydrogen bonds, and replacing the anomeric atom. The chemical synthesis was carried out by using various methods and discussed in details. The neuritogenic activities of

  为了寻找有效的神经疗法候选人，我们设计并合成了神经节苷脂Hp-s1的各种类似物。所述修饰包括通过改变碳链长度，改变氢键的数目并替换异头原子来改变疏水性。化学合成通过使用各种方法进行并详细讨论。在人神经母细胞瘤细胞系SH-SY5Y中证实了这些类似物的神经生成活性。发现神经节苷脂Hp-s1类似物比神经节苷脂Hp-s1具有更高的IL-17A转录上调活性。
• Total Syntheses of Symbioramide Derivatives from <scp>l</scp>-Serine and Their Antileukemic Activities
  作者：Hideki Azuma、Ryoko Takao、Hayato Niiro、Keiji Shikata、Seizo Tamagaki、Taro Tachibana、Kenji Ogino

  DOI：10.1021/jo0206824

  日期：2003.4.1

  Naturally occurring symbioramide, (2S,3R,2'R,3'E)-N-(2'-hydroxy-3'-octadecenoyl)-dihydrosphingosine la, was synthesized from D-erythro-dihydrosphingosine (amino part, 2) and (2R,3E)-2-hydroxy-3-octadecenoic acid (acid part, 3a), both of which were prepared from L-serine. Its diastereomer, (2S,3R,2'S,3'E)-1b, having an enantiomer of the unnatural-type acid part that was prepared from D-mannitol, and its corresponding (Z)-isomers, (2S,3R,2R,3'Z)-1c and (2S,3R,2'S,3'Z)-1d, were also prepared. The antileukemic activities of 1a-d against HL-60 and L-1210 cells were appreciated by a MTT assay. None of the four symbioramide derivatives showed antileukemic activities in HL-60 cells. In L-1210 cells, all the symbioramide derivatives showed moderate antileukemic activities. Compound 1d had the most effective activity against L-1210 cells among the four derivatives. The data suggest that unnatural types of (2'S)-isomers of acid parts are more active than those of (2R)-isomers.
• KUMAR, VIJAY;DEV, SUKH, TETRAHEDRON, 43,(1987) N 24, 5933-5948
  作者：KUMAR, VIJAY、DEV, SUKH

  DOI：——

  日期：——
• Chemistry of Ayurvedic Crude Drugs — VII11Part VI, Indian J. Chem., in press. guggulu (Resin From Commiphora Mukul) —6
  作者：Vijay Kumar、Sukh Dev

  DOI：10.1016/s0040-4020(01)87799-1

  日期：——

  With a view to elucidating the stereochemistry of quqqultetrols, components of saponified Commiphora mukul resin, D-lyxo-, L-ribo-, and L-xylo-octadecane-1,2,3,4-tetrols have been synthesised by two different routes. One method starts with D-glyceraldehyde, while the second route is based on the appropriate pentose. The absolute configuration of the natural product guggultetrol-18, has been deduced

  以阐明quqqultetrols，皂化的部件的立体化学没药穆库尔树脂，D-来苏- ，L-核糖- ，和L-木糖-octadecane -1,2,3,4-四醇已经通过两种不同的路线合成。一种方法从D-甘油醛开始，而第二种方法则基于适当的戊糖。天然产物guggultetrol-18的绝对构型，已经推导出D-木糖（2小号，3小号，4 - [R通过与合成化合物直接比较-构型）。这项工作还有助于建立古格列特20的手性。