(2S,3R,4S,5S)-3-(t-butyldimethylsilyloxy)-2,4-dimethyl-heptan-5-olide-7-carboxylic acid chloride | 1026906-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S,3R,4S,5S)-3-(t-butyldimethylsilyloxy)-2,4-dimethyl-heptan-5-olide-7-carboxylic acid chloride
• 英文别名: 2-[(2S,3S,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyl-6-oxooxan-2-yl]acetyl chloride
• CAS: 1026906-02-4
• 化学式: C₁₅H₂₇ClO₄Si
• 分子量: 334.915
• InChiKey: UBNIUPRURFTKPA-NOHGZBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S,3R,4S,5S)-3-(t-butyldimethylsilyloxy)-2,4-dimethyl-heptan-5-olide-7-carboxylic acid chloride 反应 15.0h， 以22 mg的产率得到(2S,3R,4S,5S)-3-(t-butyldimethylsilyloxy)-2,4-dimethyl-heptan-5-olide-7-carboxylic acid methyl ester
  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：

  (2S,3R,4S,5S)-3-(t-butyldimethylsilyloxy)-2,4-dimethyl-heptan-5-olide-7-carboxylic acid 在 1-氯-N,N,2-三甲基丙烯胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S,3R,4S,5S)-3-(t-butyldimethylsilyloxy)-2,4-dimethyl-heptan-5-olide-7-carboxylic acid chloride
  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