(1E,7E)-(4S,10S,12S,14R)-10,14-bis(tert-butyldimethylsilyloxy)-4-hydroxy-1-iodo-2-methyl-12-triethylsilyloxypentadeca-1,7-dien-6-one | 936445-72-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1E,7E)-(4S,10S,12S,14R)-10,14-bis(tert-butyldimethylsilyloxy)-4-hydroxy-1-iodo-2-methyl-12-triethylsilyloxypentadeca-1,7-dien-6-one
• 英文别名: (1E,4S,7E,10S,12S,14R)-10,14-bis[[tert-butyl(dimethyl)silyl]oxy]-4-hydroxy-1-iodo-2-methyl-12-triethylsilyloxypentadeca-1,7-dien-6-one
• CAS: 936445-72-6
• 化学式: C₃₄H₆₉IO₅Si₃
• 分子量: 769.08
• InChiKey: MZXQRYVPCOETFO-BRLDNIHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.95
• 重原子数：
  43
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1E,7E)-(4S,10S,12S,14R)-10,14-bis(tert-butyldimethylsilyloxy)-4-hydroxy-1-iodo-2-methyl-12-triethylsilyloxypentadeca-1,7-dien-6-one 在 二乙基甲氧基硼烷 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.25h， 以91%的产率得到(1E,7E)-(4S,6S,10S,12S,14R)-10,14-bis(tert-butyldimethylsilyloxy)-1-iodo-2-methyl-12-triethylsilyloxypentadeca-1,7-dien-4,6-diol
  参考文献：
  名称：

  Synthesis of the Monomeric Counterpart of Marinomycin A

  摘要：

  An efficient and highly convergent synthesis of the monomeric counterpart of the antitumor-antibiotic marine natural product marinomycin A was achieved by using optically active titanium complexes to control the configuration of the stereogenic centers, a highly stereo- and regioselective cross-metathesis to generate the (E)-configured C20-C21 double bond, and a Horner-Wadsworth-Emmons olefination followed by a Pd-catalyzed Stille cross-coupling to construct the tetraene moiety.

  DOI：

  10.1021/jo900945x
• 作为产物：
  描述：

  (E)-(S)-5-hydroxy-8-iodo-7-methylocta-1,7-dien-3-one 、 (4S,6S,8R)-4,8-bis(tert-butyldimethylsilyloxy)-6-triethylsilyloxynon-1-ene 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以66%的产率得到(1E,7E)-(4S,10S,12S,14R)-10,14-bis(tert-butyldimethylsilyloxy)-4-hydroxy-1-iodo-2-methyl-12-triethylsilyloxypentadeca-1,7-dien-6-one
  参考文献：
  名称：

  Synthesis of the Monomeric Counterpart of Marinomycin A

  摘要：

  An efficient and highly convergent synthesis of the monomeric counterpart of the antitumor-antibiotic marine natural product marinomycin A was achieved by using optically active titanium complexes to control the configuration of the stereogenic centers, a highly stereo- and regioselective cross-metathesis to generate the (E)-configured C20-C21 double bond, and a Horner-Wadsworth-Emmons olefination followed by a Pd-catalyzed Stille cross-coupling to construct the tetraene moiety.

  DOI：

  10.1021/jo900945x