(2S,3S,5R)-5-(tert-butyldiphenylsilanyloxy)-2,3-dihydroxydodecanoic acid ethyl ester | 1256245-92-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2S,3S,5R)-5-(tert-butyldiphenylsilanyloxy)-2,3-dihydroxydodecanoic acid ethyl ester
• 英文别名: ethyl (2S,3S,5R)-5-[tert-butyl(diphenyl)silyl]oxy-2,3-dihydroxydodecanoate
• CAS: 1256245-92-7
• 化学式: C₃₀H₄₆O₅Si
• 分子量: 514.778
• InChiKey: UFQLJOIHBHYVAT-KGPYPHOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,5R)-5-(tert-butyldiphenylsilanyloxy)-2,3-dihydroxydodecanoic acid ethyl ester 、 2,2-二甲氧基丙烷 在 CSA 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(4S,5S)-5-[(R)-2-(tert-butyldiphenylsilanyloxy)nonyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic 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：

  (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

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.