(2S,5S,6S,9S)-2,5;6,9-diepoxydecane-1,10-diol | 174645-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2S,5S,6S,9S)-2,5;6,9-diepoxydecane-1,10-diol
• 英文别名: (2S,5S,6S,9S)-2,5;6,9-diepoxydeca-1,10-diol；[(2S,5S)-5-[(2S,5S)-5-(hydroxymethyl)oxolan-2-yl]oxolan-2-yl]methanol
• CAS: 174645-23-9
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: LBBCYPJJERZPOB-XKNYDFJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5S,6S,9S)-2,5;6,9-diepoxydecane-1,10-diol 在 咪唑 、 叔丁基过氧化氢 、 草酰氯 、 Co(modp)2 、 氧气 、 L-Selectride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 为溶剂， 反应 28.67h， 生成 (5S,6S,9S,10S,13S,14S,17S)-5-tert-butyldimethylsiloxy-18-hydroxy-6,9;10,13;14,17-triepoxy-1-octadecene
  参考文献：
  名称：

  立体控制的丙酮酸丙酮酸反式-四氢呋喃单元的构建

  摘要：

  借助Sharpless AD反应和氧气氛下Co（modp）2催化的氧化环化反应，成功开发了由反式-1,5,9-癸三烯构建反式四氢呋喃（THF）单元的有效合成方法。基于这种新的合成策略，顺利地获得了无水醋酸原素中的反式-单-THF单元，反式-双-THF单元和反式-tris-THF单元。

  DOI：

  10.1016/s0957-4166(99)00259-1
• 作为产物：
  描述：

  1,5,9-decatriene 在 Hydroquinone 1,4-phthalazinediyl diether 、 potassium dioxotetrahydroxoosmate(VI) 、 Co(modp)2 叔丁基过氧化氢 、 甲基磺酰胺 、 氧气 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 异丙醇 、 叔丁醇 为溶剂， 反应 15.0h， 生成 (2S,5S,6S,9S)-2,5;6,9-diepoxydecane-1,10-diol
  参考文献：
  名称：

  Bulladecin 型乙酰生成素的简便途径 - 阿西米洛宾的全合成及其四氢呋喃段的构型校正

  摘要：

  建立了合成反式/苏式/反式-双（四氢呋喃）（THF）环单元的最有效方法，然后分十二步和十四步完成了（-）-阿西米洛宾及其非对映体的首次全合成，分别从反式 1,5,9-癸三烯，通过收敛路线，以 Wittig 反应为关键步骤。凭借这些合成结果，天然存在的阿西洛宾中双 (THF) 单元的绝对构型应该得到纠正。

  DOI：

  10.1002/(sici)1099-0690(200001)2000:2<349::aid-ejoc349>3.0.co;2-j

文献信息

• Stereochemically General Approach to Adjacent Bis(tetrahydrofuran) Cores of Annonaceous Acetogenins
  作者：Laura M. Wysocki、Matthew W. Dodge、Eric A. Voight、Steven D. Burke

  DOI：10.1021/ol062390l

  日期：2006.11.1

  A series of six 2,5-disubstituted adjacent bis(tetrahydrofuran) stereoisomers with trans/erythro/cis, trans/threo/trans, or cis/threo/cis relative stereochemistry have been synthesized from known dihydroxycyclooctenes via ring opening/cross metathesis and Pd(0)-mediated asymmetric double cycloetherification. The stereochemistry of four of these isomers has been found in the biologically active annonaceous

  通过开环/交叉复分解和Pd从已知的二羟基环辛烯合成了一系列六个具有反式/赤式/顺式，反式/苏式/反式或顺式/苏式/顺式相对立体化学的2,5-二取代的相邻双（四氢呋喃）立体异构体（0）介导的不对称双环醚化。这些异构体中的四种异构体的立体化学已在具有生物活性的非丙酮产乙酸原的天然产物中发现。[反应：请参见文字]。
• Bidirectional and Convergent Routes to oligo(Tetrahydrofurans)
  作者：Ulrich Koert、Matthias Stein、Holger Wagner

  DOI：10.1002/chem.19970030723

  日期：1997.7

  AbstractOligo(tetrahydrofurans) (oligo‐THFs) 8–12 have been synthesised stereoselectively. Multiple Williamson reactions were used as key steps. While oligo‐THFs with an even number of THF rings like the bi‐THFs 8 and 9 as well as the tetra‐THFs 10 and 11 were obtained by a bidirectional strategy, the penta‐THF 12 with an odd number of THF rings was prepared by a convergent strategy with a sulfone–aldehyde coupling as connecting step. The oligo‐THF products are important structural features of natural (Annonaceae acetogenins) and non‐natural (artificial ion channels) products.
• The synthesis of asimilobin and the correction of its tetrahydrofuran segment's configuration
  作者：Zhi-Min Wang、Shi-Kai Tian、Min Shi

  DOI：10.1016/s0040-4039(98)02577-5

  日期：1999.1

  A highly efficient synthetic method for the trans/threo/trans- bis-tetrahydrofuran (THF) ring building block was established. The title compound was synthesized in thirteen steps from trans-1,4-dichloro-2-butene via a convergent route with a Wittig reaction as the key step. The absolute configuration of the THF segment of naturally occurring asimilobin should be corrected. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of 10 stereochemically distinct bis-tetrahydrofuran intermediates for creating a library of 64 asimicin stereoisomers
  作者：Zhiyong Chen、Subhash C. Sinha

  DOI：10.1016/j.tetlet.2009.08.082

  日期：2009.11

  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.
• Wagner, Holger; Koert, Ulrich, Angewandte Chemie, 1994, vol. 106, # 18, p. 1939 - 1941
  作者：Wagner, Holger、Koert, Ulrich

  DOI：——

  日期：——