ethyl (3R)-3,7-dihydroxyheptanoate | 529510-37-0

• 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: ethyl (3R)-3,7-dihydroxyheptanoate
• CAS: 529510-37-0
• 化学式: C₉H₁₈O₄
• 分子量: 190.24
• InChiKey: FEWWOFWRWOXKME-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  ethyl (3R)-3,7-dihydroxyheptanoate 在 camphor-10-sulfonic acid 4-二甲氨基吡啶 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 tert-butyl (5R)-9-(tert-butyldiphenylsiloxy)-5-(4-methoxybenzyloxy)-3-oxononanoate
  参考文献：
  名称：

  Stereoselective synthesis of C15C24 and C25C30 fragments of dolabelides

  摘要：

  The stereocontrolled synthesis of a C15-C24 fragment of dolabelides is reported. The C19 and C21 hydroxyl-bearing stereocenters were installed using ruthenium-mediated asymmetric hydrogenations of cyclic hemiketal 4 and beta-keto ester 7. The C25-C30 portion of dolabelides was prepared as well by ring opening of chiral epoxy alcohol 12 to set up the C27 stereogenic center. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00110-2
• 作为产物：
  描述：

  ethyl (2-hydroxytetrahydropyran-2-yl)-acetate 在 ruthenium trichloride 、 氢气 、 (R)-(+)-(6,6′-二甲氧联苯-2,2′-二基)双(二苯基膦) 作用下， 以 乙醇 为溶剂， 80.0 ℃ 、999.99 kPa 条件下， 反应 25.0h， 以86%的产率得到ethyl (3R)-3,7-dihydroxyheptanoate
  参考文献：
  名称：

  Stereoselective synthesis of C15C24 and C25C30 fragments of dolabelides

  摘要：

  The stereocontrolled synthesis of a C15-C24 fragment of dolabelides is reported. The C19 and C21 hydroxyl-bearing stereocenters were installed using ruthenium-mediated asymmetric hydrogenations of cyclic hemiketal 4 and beta-keto ester 7. The C25-C30 portion of dolabelides was prepared as well by ring opening of chiral epoxy alcohol 12 to set up the C27 stereogenic center. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00110-2

文献信息

• Ruthenium-SYNPHOS-Catalyzed Asymmetric Hydrogenations: an Entry to Highly Stereoselective Synthesis of the C15−C30 Subunit of Dolabelide A
  作者：Christophe Roche、Nicolas Desroy、Mansour Haddad、Phannarath Phansavath、Jean-Pierre Genet

  DOI：10.1021/ol801493w

  日期：2008.9.1

  An efficient construction of the C15-C30 segment of the cytotoxic macrolide dolabelide A is described. The synthesis relies on ruthenium-SYNPHOS-mediated asymmetric hydrogenation reactions of beta-keto esters to generate the C19, C21, and C27 hydroxyl-bearing stereocenters with very high levels of enantio- and diastereoselectivity.
• Stereoselective synthesis of C15C24 and C25C30 fragments of dolabelides
  作者：Nicolas Desroy、Rémi Le Roux、Phannarath Phansavath、Lucia Chiummiento、Carlo Bonini、Jean-Pierre Genêt

  DOI：10.1016/s0040-4039(03)00110-2

  日期：2003.2

  The stereocontrolled synthesis of a C15-C24 fragment of dolabelides is reported. The C19 and C21 hydroxyl-bearing stereocenters were installed using ruthenium-mediated asymmetric hydrogenations of cyclic hemiketal 4 and beta-keto ester 7. The C25-C30 portion of dolabelides was prepared as well by ring opening of chiral epoxy alcohol 12 to set up the C27 stereogenic center. (C) 2003 Elsevier Science Ltd. All rights reserved.