(S,2Z,4E)-2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienenitrile | 935871-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,2Z,4E)-2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienenitrile
• 英文别名: (2Z,4E,7S)-2-bromo-7-[tert-butyl(dimethyl)silyl]oxy-7-[(1R,2R)-2-[(4-methoxyphenyl)methoxymethyl]cyclopentyl]hepta-2,4-dienenitrile
• CAS: 935871-98-0
• 化学式: C₂₇H₄₀BrNO₃Si
• 分子量: 534.609
• InChiKey: HVTDAHPONUMMQH-VROWQUCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.77
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,2Z,4E)-2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienenitrile 在 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 反应 12.5h， 生成 (3S,4S,6S,8R,10S)-((S,3E,5Z)-6-bromo-6-cyano-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hexa-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate
  参考文献：
  名称：

  Total Synthesis of Borrelidin

  摘要：

  The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11-C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segments were synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr2 center dot Et2O-mediated chelation-controlled allylation.

  DOI：

  10.1021/jo062089i
• 作为产物：
  描述：

  (S,4E)-ethyl 2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate 在 manganese(IV) oxide 、 盐酸羟胺 、 二异丁基氢化铝 、 N,N'-羰基二咪唑 作用下， 以 N-甲基吡咯烷酮 、 正己烷 、 二氯甲烷 为溶剂， 反应 52.5h， 生成 (S,2Z,4E)-2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienenitrile
  参考文献：
  名称：

  Total Synthesis of Borrelidin

  摘要：

  The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11-C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segments were synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr2 center dot Et2O-mediated chelation-controlled allylation.

  DOI：

  10.1021/jo062089i

文献信息

• Total Synthesis of Borrelidin
  作者：Tohru Nagamitsu、Daisuke Takano、Kaori Marumoto、Takeo Fukuda、Kentaro Furuya、Kazuhiko Otoguro、Kazuyoshi Takeda、Isao Kuwajima、Yoshihiro Harigaya、Satoshi Ōmura

  DOI：10.1021/jo062089i

  日期：2007.4.1

  The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11-C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segments were synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr2 center dot Et2O-mediated chelation-controlled allylation.