(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-phthalimido-octadecan-4-yl thiobenzoate | 1094213-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-phthalimido-octadecan-4-yl thiobenzoate
• 英文别名: S-[(2S,3S,4R)-1-[tert-butyl(diphenyl)silyl]oxy-2-(1,3-dioxoisoindol-2-yl)-3-hydroxyoctadecan-4-yl] benzenecarbothioate
• CAS: 1094213-82-7
• 化学式: C₄₉H₆₃NO₅SSi
• 分子量: 806.194
• InChiKey: HCXWRPKNYAEDNS-BKXXXTAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.62
• 重原子数：
  57
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  硫代苯甲酸 、 (2S,3S,4S)-1-(tert-butyldiphenylsilyloxy)-2-phthalimido-3,4-O-sulfuryl-octadecane-3,4-diol 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以87%的产率得到(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-phthalimido-octadecan-4-yl thiobenzoate
  参考文献：
  名称：

  An Efficient and General Enantioselective Synthesis of Sphingosine, Phythosphingosine, and 4-Substituted Derivatives

  摘要：

  A general and efficient protocol for the enantloselective synthesis of sphingosine, phythosphingosine, and 4-substituted derivatives was established. These compounds were obtained from a common intermediate prepared from butadiene monoepoxide by a synthetic sequence Involving enantioselective allylic substitution, cross-metathesis, and dihydroxylation.

  DOI：

  10.1021/ol802379b

文献信息

• An Efficient and General Enantioselective Synthesis of Sphingosine, Phythosphingosine, and 4-Substituted Derivatives
  作者：Josep Llaveria、Yolanda Díaz、M. Isabel Matheu、Sergio Castillón

  DOI：10.1021/ol802379b

  日期：2009.1.1

  A general and efficient protocol for the enantloselective synthesis of sphingosine, phythosphingosine, and 4-substituted derivatives was established. These compounds were obtained from a common intermediate prepared from butadiene monoepoxide by a synthetic sequence Involving enantioselective allylic substitution, cross-metathesis, and dihydroxylation.