(2R,3S)-2-(4-(benzyloxy)phenyl)-N-(4-((tert-butyldimethylsilyl)oxy)butyl)-5-((E)-3-((4-((tert-butyldimethylsilyl)oxy)butyl)amino)-3-oxoprop-1-en-1-yl)-2,3-dihydrobenzofuran-3-carboxamide | 1297604-45-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (2R,3S)-2-(4-(benzyloxy)phenyl)-N-(4-((tert-butyldimethylsilyl)oxy)butyl)-5-((E)-3-((4-((tert-butyldimethylsilyl)oxy)butyl)amino)-3-oxoprop-1-en-1-yl)-2,3-dihydrobenzofuran-3-carboxamide
• 英文别名: (2R,3S)-N-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-5-[(E)-3-[4-[tert-butyl(dimethyl)silyl]oxybutylamino]-3-oxoprop-1-enyl]-2-(4-phenylmethoxyphenyl)-2,3-dihydro-1-benzofuran-3-carboxamide
• CAS: 1297604-45-5
• 化学式: C₄₅H₆₆N₂O₆Si₂
• 分子量: 787.2
• InChiKey: SPNSNRMZRFXNQT-HRAIVHSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.33
• 重原子数：
  55
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  95.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-(4-(benzyloxy)phenyl)-N-(4-((tert-butyldimethylsilyl)oxy)butyl)-5-((E)-3-((4-((tert-butyldimethylsilyl)oxy)butyl)amino)-3-oxoprop-1-en-1-yl)-2,3-dihydrobenzofuran-3-carboxamide 在 氟化铵 、 三氯化硼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 45.0h， 生成 aperidine
  参考文献：
  名称：

  Enantioselective Total Synthesis of Aperidine

  摘要：

  An efficient total synthesis of aperidine was accomplished using a Rh-catalyzed C-H insertion of a cis-dihydrobenzofuran ring. To circumvent the facile epimerization of the cis-dihydrobenzofuran ring, we designed and prepared the C-H insertion precursor diazoamide by Raines' protocol. Finally, the efficient incorporation of a guanidine group and mild deprotection conditions yielded this labile natural product.

  DOI：

  10.1021/ol200728w
• 作为产物：
  描述：

  (E)-3-(4-((4-(benzyloxy)benzyl)oxy)-3-(2-((4-((tert-butyldimethylsilyl)oxy)butyl)amino)-1-diazo-2-oxoethyl)phenyl)-N-(4-((tert-butyldimethylsilyl)oxy)butyl)acrylamide 在 dirhodium(II) tetrakis[(S)-N-phthaloyl-tert-leucinate] 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以103 mg的产率得到(2R,3S)-2-(4-(benzyloxy)phenyl)-N-(4-((tert-butyldimethylsilyl)oxy)butyl)-5-((E)-3-((4-((tert-butyldimethylsilyl)oxy)butyl)amino)-3-oxoprop-1-en-1-yl)-2,3-dihydrobenzofuran-3-carboxamide
  参考文献：
  名称：

  Enantioselective Total Synthesis of Aperidine

  摘要：

  An efficient total synthesis of aperidine was accomplished using a Rh-catalyzed C-H insertion of a cis-dihydrobenzofuran ring. To circumvent the facile epimerization of the cis-dihydrobenzofuran ring, we designed and prepared the C-H insertion precursor diazoamide by Raines' protocol. Finally, the efficient incorporation of a guanidine group and mild deprotection conditions yielded this labile natural product.

  DOI：

  10.1021/ol200728w

文献信息

• Enantioselective Total Synthesis of Aperidine
  作者：Toshiyuki Wakimoto、Kakeru Miyata、Hitoshi Ohuchi、Tomohiro Asakawa、Haruo Nukaya、Yoshihide Suwa、Toshiyuki Kan

  DOI：10.1021/ol200728w

  日期：2011.5.20

  An efficient total synthesis of aperidine was accomplished using a Rh-catalyzed C-H insertion of a cis-dihydrobenzofuran ring. To circumvent the facile epimerization of the cis-dihydrobenzofuran ring, we designed and prepared the C-H insertion precursor diazoamide by Raines' protocol. Finally, the efficient incorporation of a guanidine group and mild deprotection conditions yielded this labile natural product.