(3S,5R)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxyhexanal | 1191384-97-0

• 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: (3S,5R)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxyhexanal
• 英文别名: (3S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-3-triethylsilyloxyhexanal
• CAS: 1191384-97-0
• 化学式: C₁₈H₄₀O₃Si₂
• 分子量: 360.685
• InChiKey: JFMBNZFDLYFIJB-IAGOWNOFSA-N

物化性质

• 沸点：
  372.7±37.0 °C(predicted)
• 密度：
  0.884±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,5R)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxyhexanal 、 氯丙烯镁 在 Cp((R,R)-TADDOL)TiCl 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.0h， 以75%的产率得到(4S,6R,8R)-8-tert-butyldimethylsilyloxy-6-triethylsilyloxynon-1-en-4-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：

  (4R,6R)-6-(tert-butyldimethylsilyloxy)-4-triethylsilyloxyhept-1-ene 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 3.0h， 生成 (3S,5R)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxyhexanal
  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.