| 1197370-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• CAS: 1197370-42-5
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: LBBCYPJJERZPOB-UTINFBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  在 水 作用下， 生成
  参考文献：
  名称：

  Synthesis of 10 stereochemically distinct bis-tetrahydrofuran intermediates for creating a library of 64 asimicin stereoisomers

  摘要：

  Stereoselective synthesis of 10 unique bifunctional stereoisomeric adjacent bis-THF intermediates (R = Bz), including 5.1-5.4, 5.7-5.9, 5.11, and 5.15-5.16, of 16 possible compounds, is described. The key steps used in the synthesis of these compounds included the rhenium(VII) oxide-mediated and the Co(modP)(2)-catalyzed trans oxidative cyclizations (OCs), the OsO4-catalyzed cis OC, and the Williamson's type etherification reactions. The remaining six bis-THF intermediates (R = Bn) can be prepared from 5.7-5.9, 5.11, and 5.15-5.16 (R = Bz) in two steps, including protection of the free alcohol as benzyl ether followed by the benzoate deprotection. These intermediates should provide access to all 64 asimicin stereoisomers; and their analogs. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.08.082

文献信息

• Catalytic Enantioselective Peroxidation of α,β-Unsaturated Aldehydes for the Asymmetric Synthesis of Biologically Important Chiral Endoperoxides
  作者：Lin Hu、Xiaojie Lu、Li Deng

  DOI：10.1021/jacs.5b05345

  日期：2015.7.8

  features an unprecedented cyclization cascade of a chiral bis(epoxy)hydroperoxide. The new methodology and synthetic strategy established in this work should be applicable to the enantioselective synthesis of a broad range of chiral 1,2-dioxolanes and 1,2-dioxanes, thereby facilitating biological and medicinal chemistry studies of peroxy natural products.

  我们开发了一种前所未有的高度对映选择性催化过氧化烯醛。这一发展的关键是发现改变氢过氧化物的结构对有机催化不对称过氧化的对映选择性有显着影响。这种新的转化使得开发了一种对映选择性路线，通向抗癌天然产物 stolonoxide 家族所有成员共享的核心结构，即连接的反式-3,6-二取代-1,2-二恶烷和反式-2,5-二取代-四氢呋喃环系。我们的路线还具有前所未有的手性双（环氧）氢过氧化物环化级联。在这项工作中建立的新方法和合成策略应适用于广泛范围的手性 1,2-二氧戊环和 1,2-二氧六环的对映选择性合成，