(S)-3-(tert-butyldimethylsilanyloxy)pent-4-enoic acid (R)-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl)octyl ester | 1251927-23-7

• 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)-3-(tert-butyldimethylsilanyloxy)pent-4-enoic acid (R)-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl)octyl ester
• 英文别名: (S)-{(R)-1-[(4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]nonan-2-yl} 3-(tert-butyldimethylsilyloxy)pent-4-enoate；[(2R)-1-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]nonan-2-yl] (3S)-3-[tert-butyl(dimethyl)silyl]oxypent-4-enoate
• CAS: 1251927-23-7
• 化学式: C₂₇H₅₀O₅Si
• 分子量: 482.776
• InChiKey: PINAABWPEVPHAB-YCAMKHIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  33
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-(tert-butyldimethylsilanyloxy)pent-4-enoic acid (R)-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl)octyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 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
• 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 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 40.58h， 生成 (S)-3-(tert-butyldimethylsilanyloxy)pent-4-enoic acid (R)-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl)octyl ester
  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 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.
• 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.