(S)-4-hydroxy-hex-5-enoic acid (1R,3S)-3-hydroxy-1-methyl-pent-4-enyl ester | 1189520-79-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-4-hydroxy-hex-5-enoic acid (1R,3S)-3-hydroxy-1-methyl-pent-4-enyl ester
• 英文别名: (S)-((2R,4S)-4'-hydroxyhex-5-en-2-yl) 4-hydroxyhex-5-enoate；[(2R,4S)-4-hydroxyhex-5-en-2-yl] (4S)-4-hydroxyhex-5-enoate
• CAS: 1189520-79-3
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: ZQCLADKIABFFOM-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  (S)-4-hydroxy-hex-5-enoic acid (1R,3S)-3-hydroxy-1-methyl-pent-4-enyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以68%的产率得到stagonolide C
  参考文献：
  名称：

  Stagonolide C的立体选择性全合成和Modiolide A的正式全合成

  摘要：

  研究了 C4 和 C7 上的保护基团对闭环复分解反应的影响。匹配诱导导致了司他内酯 C 的全合成和 modiolide A 的正式全合成。

  DOI：

  10.1055/s-0029-1217556
• 作为产物：
  描述：

  (-)-(S)-3-hydroxypent-4-enoic acid methoxymethylamide 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 氟化氢吡啶 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 22.0h， 生成 (S)-4-hydroxy-hex-5-enoic acid (1R,3S)-3-hydroxy-1-methyl-pent-4-enyl ester
  参考文献：
  名称：

  Stereoselective total synthesis of stagonolide-C

  摘要：

  The highly stereoselective synthesis of a biologically active stagonolide-C has been described. The pivotal functionalities are derived from Barbier allylation, an epoxidation by m-CPBA, a chiral-auxiliary mediated acetate aldol addition, a 1,3-anti-reduction, a Sharpless kinetic resolution, a Yamaguchi macrolactonization, and ring-closing metathesis. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.015

文献信息

• Chemo-enzymatic asymmetric total synthesis of stagonolide-C
  作者：Nandan Jana、Tridib Mahapatra、Samik Nanda

  DOI：10.1016/j.tetasy.2009.10.007

  日期：2009.11

  The naturally occurring phytotoxic noneolide stagonolide-C has been synthesized by a chemo-enzymatic approach. Two key intermediates have been synthesized by applying a metal-enzyme combined DKR (dynamic kinetic resolution) strategy, followed by RCM (ring-closing metathesis) to afford the target compound in an efficient way. (C) 2009 Elsevier Ltd. All rights reserved.
• Stereoselective total synthesis of stagonolide-C
  作者：Akkaladevi Venkatesham、Kommu Nagaiah

  DOI：10.1016/j.tetasy.2012.07.015

  日期：2012.8

  The highly stereoselective synthesis of a biologically active stagonolide-C has been described. The pivotal functionalities are derived from Barbier allylation, an epoxidation by m-CPBA, a chiral-auxiliary mediated acetate aldol addition, a 1,3-anti-reduction, a Sharpless kinetic resolution, a Yamaguchi macrolactonization, and ring-closing metathesis. (c) 2012 Elsevier Ltd. All rights reserved.
• Stereoselective Total Synthesis of Stagonolide C and Formal Total Synthesis of Modiolide A
  作者：Debendra Mohapatra、J. Yadav、Uttam Dash、P. Naidu

  DOI：10.1055/s-0029-1217556

  日期：2009.8

  The influence of protecting groups at C4 and C7 on a ring-closing metathesis reaction was investigated. Matched induction led to the total synthesis of stagonolide C and the formal total synthesis of modiolide A.

  研究了 C4 和 C7 上的保护基团对闭环复分解反应的影响。匹配诱导导致了司他内酯 C 的全合成和 modiolide A 的正式全合成。