2,2-dimethyl-5-[(1E,3E,5E,7E,13E)-(10S,12S,16S,18S,20R)-10,12,16,20-tetrakis(tert-butyldimethylsilyloxy)-8-methyl-18-triethylsilyloxyhenicosa-1,3,5,7,13-pentaenyl]-1,3-benzodioxin-4-one | 936445-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2,2-dimethyl-5-[(1E,3E,5E,7E,13E)-(10S,12S,16S,18S,20R)-10,12,16,20-tetrakis(tert-butyldimethylsilyloxy)-8-methyl-18-triethylsilyloxyhenicosa-1,3,5,7,13-pentaenyl]-1,3-benzodioxin-4-one
• 英文别名: 2,2-dimethyl-5-[(1E,3E,5E,7E,10S,12S,13E,16S,18S,20R)-10,12,16,20-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-8-methyl-18-triethylsilyloxyhenicosa-1,3,5,7,13-pentaenyl]-1,3-benzodioxin-4-one
• CAS: 936445-75-9
• 化学式: C₆₂H₁₁₄O₈Si₅
• 分子量: 1128.01
• InChiKey: DTFANGRXZXAHCQ-MTSMAVCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.52
• 重原子数：
  75
• 可旋转键数：
  32
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-[(1E,3E,5E,7E,13E)-(10S,12S,16S,18S,20R)-10,12,16,20-tetrakis(tert-butyldimethylsilyloxy)-8-methyl-18-triethylsilyloxyhenicosa-1,3,5,7,13-pentaenyl]-1,3-benzodioxin-4-one 、 sodium methylate 以 甲醇 为溶剂， 反应 1.0h， 以86%的产率得到methyl 2-hydroxy-6-[(1E,3E,5E,7E,13E)-(10S,12S,16S,18S,20R)-10,12,16,20-tetrakis(tert-butyldimethylsilyloxy)-8-methyl-18-triethylsilyloxyhenicosa-1,3,5,7,13-pentaenyl]benzoate
  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：

  5-[(1E,3E,5E)-6-(tributylstannyl)hexa-1,3,5-trienyl]-2,2-dimethyl-4H-benzo[1,3]dioxin-4-one 、 (1E,7E)-(4S,6S,10S,12S,14R)-4,6,10,14-tetrakis(tert-butyldimethylsilyloxy)-1-iodo-2-methyl-12-triethylsiloxypentadeca-1,7-diene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三苯胂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以59%的产率得到2,2-dimethyl-5-[(1E,3E,5E,7E,13E)-(10S,12S,16S,18S,20R)-10,12,16,20-tetrakis(tert-butyldimethylsilyloxy)-8-methyl-18-triethylsilyloxyhenicosa-1,3,5,7,13-pentaenyl]-1,3-benzodioxin-4-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

文献信息

• Synthesis of the Monomeric Counterpart of Marinomycin A
  作者：Dominique Amans、Laurianne Bareille、Véronique Bellosta、Janine Cossy

  DOI：10.1021/jo900945x

  日期：2009.10.16

  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.