ethyl (2Z,4E,7S)-7-(tert-butyldimethylsilyloxy)-8-(trityloxy)octa-2,4-dienoate | 863921-79-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: ethyl (2Z,4E,7S)-7-(tert-butyldimethylsilyloxy)-8-(trityloxy)octa-2,4-dienoate
• 英文别名: ethyl (2Z,4E,7S)-7-[tert-butyl(dimethyl)silyl]oxy-8-trityloxyocta-2,4-dienoate
• CAS: 863921-79-3
• 化学式: C₃₅H₄₄O₄Si
• 分子量: 556.817
• InChiKey: FIHZWDFSYIMKCI-RJBAHQDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.45
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 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：

  ethyl (2Z,4E,7S)-7-(tert-butyldimethylsilyloxy)-8-(trityloxy)octa-2,4-dienoate 在 甲酸 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 1.0h， 生成 ethyl (2Z,4E,7S,8E)-7-[tert-butyl(dimethyl)silyl]oxy-10-oxodeca-2,4,8-trienoate
  参考文献：
  名称：

  A convergent and stereoselective synthesis of a seco-precursor of macrolactin A

  摘要：

  A seco-precursor of macrolactin A was synthesized by coupling two advanced segments. Wittig reaction and Horner-Emmons reaction were utilized to construct the three characteristic E,Z and E,E dienes. The C-1-C-10 segment was synthesized through Horner-Emmons reaction with phosphonate reagent. The a-alkylation of sulfone stabilized anion with allyl bromide followed by desulfonation gave the C-11-C-24 segment. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.106
• 作为产物：
  描述：

  ethyl (E,5S)-5-hydroxy-6-trityloxyhex-2-enoate 在 草酰氯 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 7.09h， 生成 ethyl (2Z,4E,7S)-7-(tert-butyldimethylsilyloxy)-8-(trityloxy)octa-2,4-dienoate
  参考文献：
  名称：

  A convergent and stereoselective synthesis of a seco-precursor of macrolactin A

  摘要：

  A seco-precursor of macrolactin A was synthesized by coupling two advanced segments. Wittig reaction and Horner-Emmons reaction were utilized to construct the three characteristic E,Z and E,E dienes. The C-1-C-10 segment was synthesized through Horner-Emmons reaction with phosphonate reagent. The a-alkylation of sulfone stabilized anion with allyl bromide followed by desulfonation gave the C-11-C-24 segment. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.106

文献信息

• A convergent and stereoselective synthesis of a seco-precursor of macrolactin A
  作者：Shukun Li、Xiangshu Xiao、Xuebin Yan、Xuejun Liu、Rui Xu、Donglu Bai

  DOI：10.1016/j.tet.2005.07.106

  日期：2005.11

  A seco-precursor of macrolactin A was synthesized by coupling two advanced segments. Wittig reaction and Horner-Emmons reaction were utilized to construct the three characteristic E,Z and E,E dienes. The C-1-C-10 segment was synthesized through Horner-Emmons reaction with phosphonate reagent. The a-alkylation of sulfone stabilized anion with allyl bromide followed by desulfonation gave the C-11-C-24 segment. (c) 2005 Elsevier Ltd. All rights reserved.