(Z)-(R)-5-(tert-butyldiphenylsilanyloxy)dodec-2-enoic acid ethyl ester | 1256245-91-6

• 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: (Z)-(R)-5-(tert-butyldiphenylsilanyloxy)dodec-2-enoic acid ethyl ester
• 英文别名: ethyl (Z,5R)-5-[tert-butyl(diphenyl)silyl]oxydodec-2-enoate
• CAS: 1256245-91-6
• 化学式: C₃₀H₄₄O₃Si
• 分子量: 480.763
• InChiKey: SEJCMSBQFNZZKT-UBWSJTQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-(R)-5-(tert-butyldiphenylsilanyloxy)dodec-2-enoic acid ethyl ester 在 甲基磺酰胺 、 AD-mix-α 、 水 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以78%的产率得到(2S,3S,5R)-5-(tert-butyldiphenylsilanyloxy)-2,3-dihydroxydodecanoic acid ethyl ester
  参考文献：
  名称：

  First asymmetric synthesis of achaetolide

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2010.07.026
• 作为产物：
  描述：

  (R)-3-(tert-butyldiphenylsilanyloxy)decanal 、 二苯氧基磷基乙酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.45h， 以88%的产率得到(Z)-(R)-5-(tert-butyldiphenylsilanyloxy)dodec-2-enoic acid ethyl ester
  参考文献：
  名称：

  First asymmetric synthesis of achaetolide

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2010.07.026

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.