achaetolide C6,C7-O-acetonide | 1190718-68-3

• 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: achaetolide C6,C7-O-acetonide
• 英文别名: (3aS,5R,9S,11aR,E)-5-heptyl-9-hydroxy-2,2-dimethyl-4,5,8,9-tetrahydro-3aH-[1,3]dioxolo[4,5-d]oxecin-7(11aH)-one；(3aS,5R,9S,10E,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: 1190718-68-3
• 化学式: C₁₉H₃₂O₅
• 分子量: 340.46
• InChiKey: QJQMSAFKSAQEGS-MJGYBZEVSA-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

• 作为反应物：
  描述：

  achaetolide C6,C7-O-acetonide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到achaetolide
  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
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 potassium tert-butylate 、 四丁基氟化铵 、 二异丁基氢化铝 、 对甲苯磺酸 、 magnesium 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 55.33h， 生成 achaetolide C6,C7-O-acetonide
  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

• 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.
• 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.
• Absolute stereochemistry and conformational analysis of achaetolide isolated from Ophiobolus sp.
  作者：Wilanfranco Caballero Tayone、Saori Shindo、Takanori Murakami、Masaru Hashimoto、Kazuaki Tanaka、Noboru Takada

  DOI：10.1016/j.tet.2009.07.005

  日期：2009.9

  Achaetolide, as reported by Bodo et al. in 1983, was isolated from a fermentation broth of Ophiobolus sp. We established the absolute stereochemistry of achaetolide to be 3S,6R,7S,9R by way of relative stereochemical assignment with H-1 NMR analyses employing the corresponding acetonide, determination of C3 and C9 stereochemistries by an extended Mosher method. (C) 2009 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.