(3S,4S,6S,8R,10S)-((S,3E,5Z)-6-iodo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate | 935872-76-7

• 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: (3S,4S,6S,8R,10S)-((S,3E,5Z)-6-iodo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate
• 英文别名: [(1S,3E,5Z)-6-iodo-1-[(1R,2R)-2-[(4-methoxyphenyl)methoxymethyl]cyclopentyl]-7-tri(propan-2-yl)silyloxyhepta-3,5-dienyl] (3S,4S,6S,8R,10S)-3-[tert-butyl(dimethyl)silyl]oxy-11-hydroxy-4,6,8,10-tetramethylundecanoate
• CAS: 935872-76-7
• 化学式: C₅₁H₉₁IO₇Si₂
• 分子量: 999.355
• InChiKey: WKVLKARLDHHDNG-BEXZPWJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.48
• 重原子数：
  61
• 可旋转键数：
  30
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,4S,6S,8R,10S)-((S,3E,5Z)-6-iodo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以82%的产率得到(3S,4S,6S,8R,10S)-((S,3E,5Z)-6-iodo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-oxoundecanoate
  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：

  (3S,4S,6S,8R,10S)-((S,3E,5Z)-7-(allyloxy)-6-iodo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-(tetrahydro-2H-pyran-2-yloxy)undecanoate 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 12.5h， 以77.4 mg的产率得到(3S,4S,6S,8R,10S)-((S,3E,5Z)-6-iodo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-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