(2S,3R,4S,5S)-7-(t-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)-2,4-dimethyl-heptane-3,5-diol | 858948-03-5

• 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: (2S,3R,4S,5S)-7-(t-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)-2,4-dimethyl-heptane-3,5-diol
• 英文别名: (2S,3R,4S,5S)-7-[tert-butyl(dimethyl)silyl]oxy-1-[(4-methoxyphenyl)methoxy]-2,4-dimethylheptane-3,5-diol
• CAS: 858948-03-5
• 化学式: C₂₃H₄₂O₅Si
• 分子量: 426.669
• InChiKey: ROKISJFAXNYURG-YHDSQAASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S)-7-(t-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)-2,4-dimethyl-heptane-3,5-diol 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 反应 0.58h， 以85%的产率得到(2S,3R,4S,5S)-7-(t-butyldimethylsilyloxy)-2,4-dimethyl-heptane-1,3,5-triol
  参考文献：
  名称：

  Development of a Third-Generation Total Synthesis of (+)-Discodermolide:  An Expedient Still−Gennari-Type Fragment Coupling Utilizing an Advanced β-Ketophosphonate

  摘要：

  A novel total synthesis of the complex polyketide discodermolide, a promising anticancer agent of marine sponge origin, has been completed in 11.1% overall yield over 21 linear steps. This third-generation approach features an unprecedented Still-Gennari-type HWE olefination reaction between advanced C1-C8 beta-ketophosphonate 61 and C9-C24 aldehyde 7, introducing the (8z)alkene with 10:1 selectivity. The stereotetrad found in the C1-C8 subunit 61 was established via a highly diastereoselective boron-mediated aldol reaction/in situ reduction between ketone (S)-8 and 3-benzyloxypropanal. The (7S)-configuration was installed by the reduction of enone 73 with K-Selectride.

  DOI：

  10.1021/jo050481a
• 作为产物：
  描述：

  3-(叔丁基-二甲基-硅烷基OXY)-丙醛 、 (S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one 在 氯代二环己基硼烷 、 三乙胺 、 锂硼氢 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 9.0h， 以84%的产率得到(2S,3R,4S,5S)-7-(t-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)-2,4-dimethyl-heptane-3,5-diol
  参考文献：
  名称：

  Development of a Third-Generation Total Synthesis of (+)-Discodermolide:  An Expedient Still−Gennari-Type Fragment Coupling Utilizing an Advanced β-Ketophosphonate

  摘要：

  A novel total synthesis of the complex polyketide discodermolide, a promising anticancer agent of marine sponge origin, has been completed in 11.1% overall yield over 21 linear steps. This third-generation approach features an unprecedented Still-Gennari-type HWE olefination reaction between advanced C1-C8 beta-ketophosphonate 61 and C9-C24 aldehyde 7, introducing the (8z)alkene with 10:1 selectivity. The stereotetrad found in the C1-C8 subunit 61 was established via a highly diastereoselective boron-mediated aldol reaction/in situ reduction between ketone (S)-8 and 3-benzyloxypropanal. The (7S)-configuration was installed by the reduction of enone 73 with K-Selectride.

  DOI：

  10.1021/jo050481a

文献信息

• Development of a Third-Generation Total Synthesis of (+)-Discodermolide:  An Expedient Still−Gennari-Type Fragment Coupling Utilizing an Advanced β-Ketophosphonate
  作者：Ian Paterson、Isabelle Lyothier

  DOI：10.1021/jo050481a

  日期：2005.7.1

  A novel total synthesis of the complex polyketide discodermolide, a promising anticancer agent of marine sponge origin, has been completed in 11.1% overall yield over 21 linear steps. This third-generation approach features an unprecedented Still-Gennari-type HWE olefination reaction between advanced C1-C8 beta-ketophosphonate 61 and C9-C24 aldehyde 7, introducing the (8z)alkene with 10:1 selectivity. The stereotetrad found in the C1-C8 subunit 61 was established via a highly diastereoselective boron-mediated aldol reaction/in situ reduction between ketone (S)-8 and 3-benzyloxypropanal. The (7S)-configuration was installed by the reduction of enone 73 with K-Selectride.