(2S,3S)-2,3-O-isopropylidenedodecane-1,2,3-triol | 475654-33-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S)-2,3-O-isopropylidenedodecane-1,2,3-triol
• 英文别名: (2S,3S)-2,3-O-isopropylidene-1,2,3-dodecantriol；(2S,3S)-2,3-(isopropylidenedioxy)dodecan-1-ol
• CAS: 475654-33-2
• 化学式: C₁₅H₃₀O₃
• 分子量: 258.401
• InChiKey: PTECYKDCXAAZIV-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  18.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,3-O-isopropylidenedodecane-1,2,3-triol 在 吡啶 、 盐酸 、 正丁基锂 、 potassium carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 83.0h， 生成 (9S,10S)-9-hydroxynonadec-6-yn-10-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis of chiral alkenyl epoxides: the sex pheromone of the elm spanworm Ennomus subsignaria (Hübner) (Lepidoptera: Geometridae)

  摘要：

  The identification of the sex pheromone of the elm spanworm Ennomos subsignaria (Hubner), as the chiral alkenyl epoxide (6Z)-cis-9,10-epoxy-nonadecene has been accomplished. Both enantiomers of (6Z)-cis-9,10-epoxy-nonadecene have been synthesized via two routes. The key steps in the first route were to prepare both threo-epoxy tosylates and then to perform an alkylative rearrangement of these intermediates to obtain the target molecules. An alternative enantioenriched synthesis that took advantage of the Sharpless dihydroxylation reaction was developed so that a common starting material could be used to access both enantiomers. A field study and GC/EAD testing indicated that Z6-cis-9S,10R-epoxy-nonadecene was the sex pheromone of the elm spanworm E. subsignaria (Hubner). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.015
• 作为产物：
  描述：

  (-)-二甲基-2,3-邻异丙亚基-L-酒石酸酯 在 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 30% Pd/C 、 四丁基氟化铵 、 氢气 、 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， -78.0~20.0 ℃ 、344.75 kPa 条件下， 反应 24.5h， 生成 (2S,3S)-2,3-O-isopropylidenedodecane-1,2,3-triol
  参考文献：
  名称：

  Synthesis of chiral alkenyl epoxides: the sex pheromone of the elm spanworm Ennomus subsignaria (Hübner) (Lepidoptera: Geometridae)

  摘要：

  The identification of the sex pheromone of the elm spanworm Ennomos subsignaria (Hubner), as the chiral alkenyl epoxide (6Z)-cis-9,10-epoxy-nonadecene has been accomplished. Both enantiomers of (6Z)-cis-9,10-epoxy-nonadecene have been synthesized via two routes. The key steps in the first route were to prepare both threo-epoxy tosylates and then to perform an alkylative rearrangement of these intermediates to obtain the target molecules. An alternative enantioenriched synthesis that took advantage of the Sharpless dihydroxylation reaction was developed so that a common starting material could be used to access both enantiomers. A field study and GC/EAD testing indicated that Z6-cis-9S,10R-epoxy-nonadecene was the sex pheromone of the elm spanworm E. subsignaria (Hubner). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.015

文献信息

• Asymmetric dihydroxylation and one-pot epoxidation routes to (+)- and (−)-posticlure: a novel trans-epoxide as a sex pheromone component of Orgyia postica (Walker)
  作者：Rodney A Fernandes、Pradeep Kumar

  DOI：10.1016/s0040-4020(02)00685-3

  日期：2002.8

  A highly enantioselective synthesis of (+)- and (−)-posticlure has been achieved. The synthesis features the Sharpless asymmetric dihydroxylation and one-pot epoxidation as the key steps.

  已经实现了（+）-和（-）-后诱变的高度对映选择性合成。合成的关键步骤是Sharpless不对称二羟基化反应和一锅环氧化反应。
• An Efficient Synthesis of (–)-Posticlure: The Sex Pheromone ofOrgyia postica
  作者：Rodney A. Fernandes

  DOI：10.1002/ejoc.200700449

  日期：2007.10

  An efficient multigram synthesis of (–)-posticlure, the first trans-epoxide sex pheromone found in Orgyia postica, from diethyl L-tartrate is described. The synthesis was completed in seven steps and 27 % overall yield. The synthetic strategy features double-Wittig olefination and a stereoselective one-pot conversion of diol to epoxide as the key steps. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  描述了从 L-酒石酸二乙酯中高效合成 (-)-posticlure，这是在 Orgyia postica 中发现的第一种反式环氧化物性信息素。合成分七个步骤完成，总产率为 27%。该合成策略以双维蒂希烯化和二醇立体选择性一锅法转化为环氧化物为关键步骤。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)