(R)-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)nonan-2-ol | 1256245-95-0

• 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: (R)-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)nonan-2-ol
• 英文别名: (2R)-1-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]nonan-2-ol
• CAS: 1256245-95-0
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: QCZBTQQTAFQEDY-KFWWJZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)nonan-2-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 achaetolide C6,C7-O-acetonide
  参考文献：
  名称：

  使用莱伊二硫代烷基化从酒石酸对映体特异性合成功能化多元醇：在皂苷总合成中的应用

  摘要：

  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。

  DOI：

  10.1016/j.tet.2016.11.035
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 potassium tert-butylate 、 二异丁基氢化铝 、 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 34.33h， 生成 (R)-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)nonan-2-ol
  参考文献：
  名称：

  The stereoselective total synthesis of (−)-achaetolide

  摘要：

  The stereoselective total synthesis of (-)-achaetolide is described in a convergent manner. Grignard addition, Wittig homologation, acetate aldol and ring closing metathesis reactions were the key steps involved. The required olefinic alcohol fragments were synthesized from a single chiral pool material 2-deoxy-D-ribose and olefinic acid fragment was prepared from acetate aldol reaction. Both the olefinic acid and alcohols were prepared in a concise method. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.010

文献信息

• First asymmetric synthesis of achaetolide
  作者：Tapas Das、Rajib Bhuniya、Samik Nanda

  DOI：10.1016/j.tetasy.2010.07.026

  日期：2010.9

  The first asymmetric synthesis of the 10-membered macrolide achaetolide is reported in this article. The main highlight of the synthetic strategy is the ring-closing metathesis (RCM) of intermediate 19, which in turn can be accessed from coupling between alcohol 11 and acid 18. The synthesis of 11 involves enzymatic kinetic resolution (EKR) coupled with a Mitsunobu inversion strategy, while 18 can be prepared by adopting a metal-enzyme combined dynamic kinetic resolution (DKR) reaction followed by functional group manipulation. (C) 2010 Elsevier Ltd. All rights reserved.
• Stereoselective total synthesis of achaetolide and reconfirmation of its absolute configuration
  作者：P. Srihari、B. Kumaraswamy、P. Shankar、V. Ravishashidhar、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.09.070

  日期：2010.11

  The stereoselective total synthesis of achaetolide 1 has been achieved and its absolute stereochemistry has been reconfirmed to be 35,6R,7S,9R configuration. Keck allylation, Sharpless asymmetric dihydroxylation, and ring closing metathesis are the key steps involved in the target synthesis. (C) 2010 Elsevier Ltd. All rights reserved.
• The stereoselective total synthesis of (−)-achaetolide
  作者：Pallavi Thakur、Boyapelly Kumaraswamy、Gurram Raji Reddy、Rakeshwar Bandichhor、Khagga Mukkantii

  DOI：10.1016/j.tetasy.2012.03.010

  日期：2012.4

  The stereoselective total synthesis of (-)-achaetolide is described in a convergent manner. Grignard addition, Wittig homologation, acetate aldol and ring closing metathesis reactions were the key steps involved. The required olefinic alcohol fragments were synthesized from a single chiral pool material 2-deoxy-D-ribose and olefinic acid fragment was prepared from acetate aldol reaction. Both the olefinic acid and alcohols were prepared in a concise method. (C) 2012 Elsevier Ltd. All rights reserved.
• 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。