methyl (E)-4-[(4S,6R,7S,9E)-6,16-bis[[tert-butyl(dimethyl)silyl]oxy]-7-methyl-2-oxo-3-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraen-4-yl]but-2-enoate | 350794-12-6

• 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: methyl (E)-4-[(4S,6R,7S,9E)-6,16-bis[[tert-butyl(dimethyl)silyl]oxy]-7-methyl-2-oxo-3-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraen-4-yl]but-2-enoate
• CAS: 350794-12-6
• 化学式: C₃₃H₅₄O₆Si₂
• 分子量: 602.959
• InChiKey: GBFWSGGAVUNLFS-DKDHMOCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.63
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (E)-4-[(4S,6R,7S,9E)-6,16-bis[[tert-butyl(dimethyl)silyl]oxy]-7-methyl-2-oxo-3-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraen-4-yl]but-2-enoate 在 二苯基磷酸 、 三乙胺 、 三丁基氧化锡 作用下， 以 甲苯 、 苯 为溶剂， 反应 58.0h， 生成 (4S,6R,7S,9E)-6,16-bis[[tert-butyl(dimethyl)silyl]oxy]-4-[(E)-3-isocyanatoprop-2-enyl]-7-methyl-3-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraen-2-one
  参考文献：
  名称：

  Total Synthesis of (−)-Salicylihalamide A

  摘要：

  [GRAPHICS]A 16-step synthesis of the novel cytotoxin salicylihalamide A (1E) has been achieved in 3.3% overall yield using ring closing metathesis to generate the macrolide and addition of (1Z,3Z)-hexadienylcuprate (2), which was generated in situ from ethylcuprate and acetylene, to alkenyl isocyanate 3 to form the side chain.

  DOI：

  10.1021/ol015822v
• 作为产物：
  描述：

  在 2,6-二甲基吡啶 、 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 methyl (E)-4-[(4S,6R,7S,9E)-6,16-bis[[tert-butyl(dimethyl)silyl]oxy]-7-methyl-2-oxo-3-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraen-4-yl]but-2-enoate
  参考文献：
  名称：

  Total Synthesis of (−)-Salicylihalamide A

  摘要：

  [GRAPHICS]A 16-step synthesis of the novel cytotoxin salicylihalamide A (1E) has been achieved in 3.3% overall yield using ring closing metathesis to generate the macrolide and addition of (1Z,3Z)-hexadienylcuprate (2), which was generated in situ from ethylcuprate and acetylene, to alkenyl isocyanate 3 to form the side chain.

  DOI：

  10.1021/ol015822v

文献信息

• Total Synthesis of (−)-Salicylihalamide A
  作者：Barry B. Snider、Fengbin Song

  DOI：10.1021/ol015822v

  日期：2001.6.1

  [GRAPHICS]A 16-step synthesis of the novel cytotoxin salicylihalamide A (1E) has been achieved in 3.3% overall yield using ring closing metathesis to generate the macrolide and addition of (1Z,3Z)-hexadienylcuprate (2), which was generated in situ from ethylcuprate and acetylene, to alkenyl isocyanate 3 to form the side chain.