(2R,3R,4R,5S)-4-<(E)-2-(Ethoxycarbonyl)ethenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-<4-(tert-butyldimethylsilyloxy)butyl>tetrahydrofuran | 152492-07-4

• 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: (2R,3R,4R,5S)-4-<(E)-2-(Ethoxycarbonyl)ethenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-<4-(tert-butyldimethylsilyloxy)butyl>tetrahydrofuran
• CAS: 152492-07-4
• 化学式: C₂₇H₄₈O₈Si
• 分子量: 528.759
• InChiKey: PYTUVEWEWFPUKC-LULMGYOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-4-<(E)-2-(Ethoxycarbonyl)ethenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-<4-(tert-butyldimethylsilyloxy)butyl>tetrahydrofuran 在 六甲基磷酰三胺 、 samarium diiodide 、 4 A molecular sieve 、 四丁基氟化铵 、 pyridinium chlorochromate 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Total syntheses of (-)-anastrephin, (-)-epianastrephin, and their 7a-epimers: use of samarium(II) iodide-mediated intramolecular reductive coupling for the construction of their hexahydrobenzofuran-2(3H)-one skeletons

  摘要：

  D-Glucose-derived alpha,beta-unsaturated ester 17, which includes a geminally and differntially substituted gamma-carbon and a terminal aldehyde functionality, was subjected to a SMI2-Mediated intramolecular reductive coupling reaction in a THF solution containing 1/10 volume of HMPA. The reaction proceeded with moderate stereoselectivity to provide a diastereomeric mixture of hexahydrobenzofuran-2 (3H)-ones, in which cis-fused product 25 was obtained as the major isomer in 35% isolated yield. Two trans-fused coupling products 26 (17%) and 27 (14%) were also obtained. Starting from major product 25, the insect sex attractants (-)-anastrephin (1) and (-)-epianastrephin (2) were synthesized enantiospecifically. Two unnatural stereocongeners, (-)-7a-epi-anastrephin (3) and (-)-7a-epi-epianastrephin (4), were also derived from 25.

  DOI：

  10.1021/jo00075a021
• 作为产物：
  描述：

  (2R,3R,4R,5S)-2,3-(Isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-<4-(tert-butyldimethylsilyloxy)butyl>-4-vinyltetrahydrofuran 在 sodium hydride 、 臭氧 、 三苯基膦 作用下， 生成 (2R,3R,4R,5S)-4-<(E)-2-(Ethoxycarbonyl)ethenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-<4-(tert-butyldimethylsilyloxy)butyl>tetrahydrofuran
  参考文献：
  名称：

  mar（II）碘化物介导的还原环化方法可完全合成昆虫性引诱剂（-）-阿斯特拉芬

  摘要：

  在THF-HMPA中使用SmI 2有效地实现了对映体纯的γ，γ-差异C-取代的α，β-不饱和酯5的分子内还原环化，该酯具有末端醛官能团。从主要的环化产物6开始，（-）-anastrephin的对映体特异性全合成。1完成。

  DOI：

  10.1016/s0040-4039(00)74773-3