(4R,6E,8R,9R,10S,12R)-10-(tert-butyldimethylsiloxy)-16-(tert-butyldiphenylsiloxy)-8,12-(di-4-methoxybenzyloxy)-4-methoxymethoxy-6,9-dimethylhexadec-6-ene | 1052661-32-1

• 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: (4R,6E,8R,9R,10S,12R)-10-(tert-butyldimethylsiloxy)-16-(tert-butyldiphenylsiloxy)-8,12-(di-4-methoxybenzyloxy)-4-methoxymethoxy-6,9-dimethylhexadec-6-ene
• 英文别名: tert-butyl-[(E,5R,7S,8R,9R,13R)-7-[tert-butyl(dimethyl)silyl]oxy-13-(methoxymethoxy)-5,9-bis[(4-methoxyphenyl)methoxy]-8,11-dimethylhexadec-10-enoxy]-diphenylsilane
• CAS: 1052661-32-1
• 化学式: C₅₈H₈₈O₈Si₂
• 分子量: 969.503
• InChiKey: QQSYWGLIZQXIRZ-UQGDXMFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.46
• 重原子数：
  68
• 可旋转键数：
  32
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4R,6E,8R,9R,10S,12R)-10-(tert-butyldimethylsiloxy)-16-(tert-butyldiphenylsiloxy)-8,12-(di-4-methoxybenzyloxy)-4-methoxymethoxy-6,9-dimethylhexadec-6-ene 在 甲醇 、 氟化铵 作用下， 反应 72.0h， 以82%的产率得到(5R,7S,8R,9R,10E,13R)-7-(tert-butyldimethylsiloxy)-5,9-(di-4-methoxybenzyloxy)-13-methoxymethoxy-8,11-dimethylhexadec-10-en-1-ol
  参考文献：
  名称：

  Ruthenium-SYNPHOS-Catalyzed Asymmetric Hydrogenations: an Entry to Highly Stereoselective Synthesis of the C15−C30 Subunit of Dolabelide A

  摘要：

  An efficient construction of the C15-C30 segment of the cytotoxic macrolide dolabelide A is described. The synthesis relies on ruthenium-SYNPHOS-mediated asymmetric hydrogenation reactions of beta-keto esters to generate the C19, C21, and C27 hydroxyl-bearing stereocenters with very high levels of enantio- and diastereoselectivity.

  DOI：

  10.1021/ol801493w
• 作为产物：
  描述：

  (4R,6E,8R,9R,10S,12R)-10-(tert-butyldimethylsiloxy)-16-(tert-butyldiphenylsiloxy)-12-(4-methoxybenzyloxy)-4-methoxymethoxy-6,9-dimethylhexadec-6-en-8-ol 、 2,2,2-三氯代亚氨逐乙酸-4-甲氧基苄酯 在 lanthanum(lll) triflate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以84%的产率得到(4R,6E,8R,9R,10S,12R)-10-(tert-butyldimethylsiloxy)-16-(tert-butyldiphenylsiloxy)-8,12-(di-4-methoxybenzyloxy)-4-methoxymethoxy-6,9-dimethylhexadec-6-ene
  参考文献：
  名称：

  Ruthenium-SYNPHOS-Catalyzed Asymmetric Hydrogenations: an Entry to Highly Stereoselective Synthesis of the C15−C30 Subunit of Dolabelide A

  摘要：

  An efficient construction of the C15-C30 segment of the cytotoxic macrolide dolabelide A is described. The synthesis relies on ruthenium-SYNPHOS-mediated asymmetric hydrogenation reactions of beta-keto esters to generate the C19, C21, and C27 hydroxyl-bearing stereocenters with very high levels of enantio- and diastereoselectivity.

  DOI：

  10.1021/ol801493w

文献信息

• Ruthenium-SYNPHOS-Catalyzed Asymmetric Hydrogenations: an Entry to Highly Stereoselective Synthesis of the C15−C30 Subunit of Dolabelide A
  作者：Christophe Roche、Nicolas Desroy、Mansour Haddad、Phannarath Phansavath、Jean-Pierre Genet

  DOI：10.1021/ol801493w

  日期：2008.9.1

  An efficient construction of the C15-C30 segment of the cytotoxic macrolide dolabelide A is described. The synthesis relies on ruthenium-SYNPHOS-mediated asymmetric hydrogenation reactions of beta-keto esters to generate the C19, C21, and C27 hydroxyl-bearing stereocenters with very high levels of enantio- and diastereoselectivity.