(1RS,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-1-phenylselenyl-16-oxabicyclo[13.2.2]nonadeca-3,8,10-triene-17,18-dione | 640270-74-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (1RS,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-1-phenylselenyl-16-oxabicyclo[13.2.2]nonadeca-3,8,10-triene-17,18-dione
• 英文别名: (3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-1-phenylselanyl-16-oxabicyclo[13.2.2]nonadeca-3,8,10-triene-17,18-dione
• CAS: 640270-74-2
• 化学式: C₃₃H₃₈O₆Se
• 分子量: 609.621
• InChiKey: OSTVJFHCUUZFME-QPEZXGRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1RS,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-1-phenylselenyl-16-oxabicyclo[13.2.2]nonadeca-3,8,10-triene-17,18-dione 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以118 mg的产率得到(1EZ,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-16-oxabicyclo[13.2.2]nonadeca-1,3,8,10-17,18-dione
  参考文献：
  名称：

  Total Synthesis of (+)-Macquarimicin A

  摘要：

  The first total synthesis of (+)-macquarimicin A (1), a novel inhibitor of neutral sphingomyelinase (N-SMase) with antiinflammatory activity, has been accomplished. The present work determined the absolute configuration of (+)-1 and revised the C(2)-C(3) geometry to be Z. The synthesis features a transannular Diels-Alder reaction, which constructed the tetracyclic framework stereoselectively, and a convergent and efficient synthetic pathway, which afforded (+)-macquarimicin A (1) in 27 steps (longest linear sequence) with 9.9% overall yield.

  DOI：

  10.1021/ja038732p
• 作为产物：
  描述：

  (2E,5R,6S,7Z,9E,12R,14R)-12,14-bis(tert-butyldimethylsilyloxy)-15-(2,2-dimethyl-1,3-dioxin-4-one-6-yl)-1-(methoxycarbonyl)oxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-2,7,9-pentadecatriene 在 吡啶 、 四(三苯基膦)钯 、 氟化氢吡啶 、 三乙胺 、 N,N-二异丙基乙胺 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 79.17h， 生成 (1RS,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-1-phenylselenyl-16-oxabicyclo[13.2.2]nonadeca-3,8,10-triene-17,18-dione
  参考文献：
  名称：

  Total Synthesis of (+)-Macquarimicin A

  摘要：

  The first total synthesis of (+)-macquarimicin A (1), a novel inhibitor of neutral sphingomyelinase (N-SMase) with antiinflammatory activity, has been accomplished. The present work determined the absolute configuration of (+)-1 and revised the C(2)-C(3) geometry to be Z. The synthesis features a transannular Diels-Alder reaction, which constructed the tetracyclic framework stereoselectively, and a convergent and efficient synthetic pathway, which afforded (+)-macquarimicin A (1) in 27 steps (longest linear sequence) with 9.9% overall yield.

  DOI：

  10.1021/ja038732p

文献信息

• Total Synthesis of (+)-Macquarimicin A
  作者：Ryosuke Munakata、Hironori Katakai、Tatsuo Ueki、Jun Kurosaka、Ken-ichi Takao、Kin-ichi Tadano

  DOI：10.1021/ja038732p

  日期：2003.12.1

  The first total synthesis of (+)-macquarimicin A (1), a novel inhibitor of neutral sphingomyelinase (N-SMase) with antiinflammatory activity, has been accomplished. The present work determined the absolute configuration of (+)-1 and revised the C(2)-C(3) geometry to be Z. The synthesis features a transannular Diels-Alder reaction, which constructed the tetracyclic framework stereoselectively, and a convergent and efficient synthetic pathway, which afforded (+)-macquarimicin A (1) in 27 steps (longest linear sequence) with 9.9% overall yield.