methyl 2-[(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]-6-triisopropylsilyloxybenzoate | 1191385-00-8

• 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: methyl 2-[(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]-6-triisopropylsilyloxybenzoate
• 英文别名: methyl 2-[(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]-6-tri(propan-2-yl)silyloxybenzoate
• CAS: 1191385-00-8
• 化学式: C₆₉H₁₃₂O₈Si₆
• 分子量: 1258.32
• InChiKey: UMOGYJKPBRPTLR-PWBCRBCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.58
• 重原子数：
  83
• 可旋转键数：
  39
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  methyl 2-[(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]-6-triisopropylsilyloxybenzoate 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 以21%的产率得到methyl 2-[(1E,3E,5E,7E,10S,12S,13E,16S,18S,20R)-10,12,16,20-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-18-hydroxy-8-methylhenicosa-1,3,5,7,13-pentaenyl]-6-tri(propan-2-yl)silyloxybenzoate
  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：

  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 、 三异丙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到methyl 2-[(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]-6-triisopropylsilyloxybenzoate
  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.