(3aS,5R,9S,10Z,11aR)-5-heptyl-9-hydroxy-2,2-dimethyl-3a,4,5,8,9,11a-hexahydro-[1,3]dioxolo[4,5-d]oxecin-7-one | 1251927-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: (3aS,5R,9S,10Z,11aR)-5-heptyl-9-hydroxy-2,2-dimethyl-3a,4,5,8,9,11a-hexahydro-[1,3]dioxolo[4,5-d]oxecin-7-one
• CAS: 1251927-26-0
• 化学式: C₁₉H₃₂O₅
• 分子量: 340.46
• InChiKey: QJQMSAFKSAQEGS-AMGXLETLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-{(R)-1-[(4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]nonan-2-yl} 3-hydroxypent-4-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以23%的产率得到(3aS,5R,9S,10Z,11aR)-5-heptyl-9-hydroxy-2,2-dimethyl-3a,4,5,8,9,11a-hexahydro-[1,3]dioxolo[4,5-d]oxecin-7-one
  参考文献：
  名称：

  First total synthesis of achaetolide

  摘要：

  The first total synthesis of achaetolide, a 10-membered macrolactone was achieved using Mitsunobu reaction and Grubbs ring-closing metathesis reaction as the key steps for ring construction. The desired stereo centres were generated by Jacobsen hydrolytic kinetic resolution, dihydroxylation and Sharpless asymmetric epoxidation reactions. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.127

文献信息

• Enantiospecific synthesis of functionalized polyols from tartaric acid using Ley's dithiaketalization: Application to the total synthesis of achaetolide
  作者：Amit K. Bali、Sunil Kumar Sunnam、Kavirayani R. Prasad

  DOI：10.1016/j.tet.2016.11.035

  日期：2016.12

  Synthesis of chiral tetrols and 1,2,4-triols with varied substitutions was accomplished from tartaric acid. Pivotal reaction in the synthesis was the use of Ley's dithianylation of an alkynyl ketone derived from tartaric acid. Application of the strategy was demonstrated in the total synthesis of decanolactone achaetolide.

  由酒石酸合成具有不同取代基的手性四醇和1,2,4-三醇。合成中的关键反应是使用莱特对酒石酸衍生的炔基酮进行二噻烷基化。该策略在癸内酯癸内酯全合成中得到了证明。
• First total synthesis of achaetolide
  作者：S. Chandrasekhar、S.V. Balaji、G. Rajesh

  DOI：10.1016/j.tetlet.2010.07.127

  日期：2010.9

  The first total synthesis of achaetolide, a 10-membered macrolactone was achieved using Mitsunobu reaction and Grubbs ring-closing metathesis reaction as the key steps for ring construction. The desired stereo centres were generated by Jacobsen hydrolytic kinetic resolution, dihydroxylation and Sharpless asymmetric epoxidation reactions. (c) 2010 Elsevier Ltd. All rights reserved.