methyl (2E,4S,7R)-7-,[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4-hydroxy-2,8-nonadienoate | 1240505-13-8

• 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: methyl (2E,4S,7R)-7-,[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4-hydroxy-2,8-nonadienoate
• 英文别名: methyl (2E,4S,7R)-7-[tert-butyl(dimethyl)silyl]oxy-4-hydroxynona-2,8-dienoate
• CAS: 1240505-13-8
• 化学式: C₁₆H₃₀O₄Si
• 分子量: 314.497
• InChiKey: PAZVMGJOKRENJQ-IRTDIPEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2E,4S,7R)-7-,[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4-hydroxy-2,8-nonadienoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以70%的产率得到methyl 2-[(2R,3S,6R)-6-ethenyl-3-hydroxyoxan-2-yl]acetate
  参考文献：
  名称：

  Stereoselective formal synthesis of aspergillide A

  摘要：

  The stereoselective formal synthesis of aspergillide A (1), a cytotoxic 14-membered macrolide, is disclosed. The key intermediate, a trisubstituted tetrahydropyran core is prepared by SmI(2)-induced intramolecular reductive cyclization as well as by using sequential alpha-aminooxylation, Homer-Wadsworth-Emmons olefination, and followed by Oxa-Michael cyclization. Other notable transformations in the synthesis include the use of Jacobsen's hydrolytic kinetic resolution, esterification, ring-closing metathesis (RCM), and cross-metathesis (CM) reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.013
• 作为产物：
  描述：

  methyl (2E,4S,7R)-4-anilinooxy-7-[tert-butyl(dimethyl)silyl]oxynona-2,8-dienoate 在 copper diacetate 作用下， 以 乙醇 为溶剂， 以85%的产率得到methyl (2E,4S,7R)-7-,[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4-hydroxy-2,8-nonadienoate
  参考文献：
  名称：

  Stereoselective formal synthesis of aspergillide A

  摘要：

  The stereoselective formal synthesis of aspergillide A (1), a cytotoxic 14-membered macrolide, is disclosed. The key intermediate, a trisubstituted tetrahydropyran core is prepared by SmI(2)-induced intramolecular reductive cyclization as well as by using sequential alpha-aminooxylation, Homer-Wadsworth-Emmons olefination, and followed by Oxa-Michael cyclization. Other notable transformations in the synthesis include the use of Jacobsen's hydrolytic kinetic resolution, esterification, ring-closing metathesis (RCM), and cross-metathesis (CM) reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.013

文献信息

• Stereoselective formal synthesis of aspergillide A
  作者：Gowravaram Sabitha、D. Vasudeva Reddy、A. Senkara Rao、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.06.013

  日期：2010.8

  The stereoselective formal synthesis of aspergillide A (1), a cytotoxic 14-membered macrolide, is disclosed. The key intermediate, a trisubstituted tetrahydropyran core is prepared by SmI(2)-induced intramolecular reductive cyclization as well as by using sequential alpha-aminooxylation, Homer-Wadsworth-Emmons olefination, and followed by Oxa-Michael cyclization. Other notable transformations in the synthesis include the use of Jacobsen's hydrolytic kinetic resolution, esterification, ring-closing metathesis (RCM), and cross-metathesis (CM) reactions. (C) 2010 Elsevier Ltd. All rights reserved.