(4S,6S,8R)-4,8-bis(tert-butyldimethylsilyloxy)-6-triethylsilyloxynon-1-yne | 1191384-94-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4S,6S,8R)-4,8-bis(tert-butyldimethylsilyloxy)-6-triethylsilyloxynon-1-yne
• 英文别名: [(2R,4S,6S)-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]non-8-yn-4-yl]oxy-triethylsilane
• CAS: 1191384-94-7
• 化学式: C₂₇H₅₈O₃Si₃
• 分子量: 515.012
• InChiKey: YRTIJUNSYSVCCY-DSITVLBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.98
• 重原子数：
  33
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,E)-6-iodo-3-(4-methoxybenzyloxy)-5-methylhex-5-enal 、 (4S,6S,8R)-4,8-bis(tert-butyldimethylsilyloxy)-6-triethylsilyloxynon-1-yne 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以18%的产率得到(E,4S,10S,12S,14R)-10,14-bis[[tert-butyl(dimethyl)silyl]oxy]-1-iodo-4-[(4-methoxyphenyl)methoxy]-2-methyl-12-triethylsilyloxypentadec-1-en-7-yn-6-ol
  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：

  (4S,6S,8R)-1,1-dibromo-4,8-bis(tert-butyldimethylsilyloxy)-6-triethylsilyloxynon-1-ene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以87%的产率得到(4S,6S,8R)-4,8-bis(tert-butyldimethylsilyloxy)-6-triethylsilyloxynon-1-yne
  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