[(2S)-hept-6-en-2-yl] 2-[(2R,3S,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-ethenyloxan-2-yl]acetate | 1240505-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: [(2S)-hept-6-en-2-yl] 2-[(2R,3S,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-ethenyloxan-2-yl]acetate
• CAS: 1240505-14-9
• 化学式: C₂₂H₄₀O₄Si
• 分子量: 396.643
• InChiKey: APDOZQIIZIMMFJ-LWYYNNOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2S)-hept-6-en-2-yl] 2-[(2R,3S,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-ethenyloxan-2-yl]acetate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到(1R,5S,9Z,11R,14S)-14-[tert-butyl(dimethyl)silyl]oxy-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one
  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：

  2-[(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]acetic acid 、 2(S)-羟基庚-6-烯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以79%的产率得到[(2S)-hept-6-en-2-yl] 2-[(2R,3S,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-ethenyloxan-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

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.