(2R,3R,4R,5S)-4-<(E)-2-(Ethoxycarbonyl)ethenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-(4-oxopentyl)tetrahydrofuran | 152492-33-6

• 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-oxopentyl)tetrahydrofuran
• CAS: 152492-33-6
• 化学式: C₂₂H₃₄O₈
• 分子量: 426.507
• InChiKey: SUPJZNMFWZWSGN-BCNZURGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  89.52
• 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-oxopentyl)tetrahydrofuran 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2R,3R,4R,5S)-4-<(E)-2-(Ethoxycarbonyl)ethenyl>-4-<(4R/S)-4-hydroxypentyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>tetrahydrofuran
  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)-4-(2-Iodoethyl)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran 在 咪唑 、 lithium aluminium tetrahydride 、 4 A molecular sieve 、 四丁基氟化铵 、 sodium hydride 、 臭氧 、 三苯基膦 、 pyridinium chlorochromate 、 sodium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成 (2R,3R,4R,5S)-4-<(E)-2-(Ethoxycarbonyl)ethenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-(4-oxopentyl)tetrahydrofuran
  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