(2S,3R)-ethyl 2,3-dihydroxynonanoate | 1001338-95-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-ethyl 2,3-dihydroxynonanoate
• 英文别名: ethyl (2S,3R)-2,3-dihydroxynonanoate
• CAS: 1001338-95-9
• 化学式: C₁₁H₂₂O₄
• 分子量: 218.293
• InChiKey: BWAASTATEBMWTP-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-ethyl 2,3-dihydroxynonanoate 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以98%的产率得到(2S,3R)-ethyl 2,3-isopropylidenedioxynonanoate
  参考文献：
  名称：

  Chiral vicinal diols as platforms for separable diastereomers in Johnson–Claisen rearrangement: a new short route to (−)-nor-canadensolide, (−)-canadensolide and (−)-sporothriolide

  摘要：

  The chiral vicinal diols prepared by asymmetric dihydroxylation in high enantioselectivities provide an excellent platform for separable diastereomers in the Johnson-Claisen rearrangement. The separated syn-diastereomers were converted into the advanced gamma-(lactone-lactol) intermediates (in six steps, 26-27% overall yields) for the synthesis of (-)-nor-canadensoiide, (-)-canadensolide and (-)-sporothriolide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.084
• 作为产物：
  描述：

  壬-2-烯酸乙酯 在 potassium osmate(VI) dihydrate 、 甲基磺酰胺 、 水 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以96%的产率得到(2S,3R)-ethyl 2,3-dihydroxynonanoate
  参考文献：
  名称：

  Synthesis of β,γ-disubstituted-γ-lactones through a Johnson–Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide

  摘要：

  The Johnson-Claisen rearrangement of allyl alcohols with chiral vicinal diol functionality was employed to access chiral beta,gamma-disubstituted-gamma-lactones in high enantio- and diastereoselectivity. These were efficiently converted into nor-canadensolide, the advanced gamma-(lactone-lactol) intermediate for xylobovide, canadensolide and sporothriolide and the lactone moiety of the santolinolides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.018

文献信息

• Multicomponent Approach to the Synthesis of Oxidized Amides through Nitrile Hydrozirconation
  作者：Shuangyi Wan、Michael E. Green、Jung-Hyun Park、Paul E. Floreancig

  DOI：10.1021/ol702184n

  日期：2007.12.1

  "Oxidized" amides, as represented by acyl aminals and acyl hemiaminals, are integral subunits of several natural products that exhibit useful biological activity. In this paper a multicomponent approach to these groups from acylimine intermediates is demonstrated. The acylimines; are accessed through a sequence of nitrile hydrozirconation and acylation, making this highly versatile amide synthesis useful for a range of applications in target- and diversity-oriented synthesis.

  氧化的酰胺（如酰胺亚胺和酰半胺）是多种具有有用生物学活性的天然产物的重要组成部分。本文展示了一种通过丙二酰亚胺中间体实现这些化学结构的多组分合成策略。这些丙二酰亚胺是通过腈的水锆化和随后的酰化过程制备的，这使得这一高度灵活的酰胺合成方法在目标导向和多样性导向的合成中得到广泛应用。
• Stereoselective Reduction of β-Hydroxy α-Ketoesters: A Concise Synthesis of<i>anti</i>-α,β-Dihydroxy Esters
  作者：Jianbo Wang、Mingyi Liao、Wengang Yao

  DOI：10.1055/s-2004-831210

  日期：——

  A new synthetic route to anti-α,β-dihydroxy esters has been developed. The new method consists of three steps starting from an aldehyde: the nucleophilic condensation with ethyl diazo­acetate, oxidation with dimethyldioxirane, and stereoselective reduction with NaBH4.

  我们开发了一种合成抗δ,δ²-二羟基酯的新方法。新方法包括三个步骤：从醛开始，与重氮乙酸乙酯进行亲核缩合，与二甲基二氧环己烷进行氧化，以及与 NaBH4 进行立体选择性还原。
• Synthesis of β,γ-disubstituted-γ-lactones through a Johnson–Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide
  作者：Rodney A. Fernandes、Arun B. Ingle、Vijay P. Chavan

  DOI：10.1016/j.tetasy.2009.11.018

  日期：2009.12

  The Johnson-Claisen rearrangement of allyl alcohols with chiral vicinal diol functionality was employed to access chiral beta,gamma-disubstituted-gamma-lactones in high enantio- and diastereoselectivity. These were efficiently converted into nor-canadensolide, the advanced gamma-(lactone-lactol) intermediate for xylobovide, canadensolide and sporothriolide and the lactone moiety of the santolinolides. (C) 2009 Elsevier Ltd. All rights reserved.
• Chiral vicinal diols as platforms for separable diastereomers in Johnson–Claisen rearrangement: a new short route to (−)-nor-canadensolide, (−)-canadensolide and (−)-sporothriolide
  作者：Rodney A. Fernandes、Arun B. Ingle

  DOI：10.1016/j.tetlet.2008.12.084

  日期：2009.3

  The chiral vicinal diols prepared by asymmetric dihydroxylation in high enantioselectivities provide an excellent platform for separable diastereomers in the Johnson-Claisen rearrangement. The separated syn-diastereomers were converted into the advanced gamma-(lactone-lactol) intermediates (in six steps, 26-27% overall yields) for the synthesis of (-)-nor-canadensoiide, (-)-canadensolide and (-)-sporothriolide. (C) 2009 Elsevier Ltd. All rights reserved.