(4S,5R)-2,2,5-Trimethyl-4-((S)-1-methylsulfanyl-propyl)-[1,3]dioxane | 138092-01-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-2,2,5-Trimethyl-4-((S)-1-methylsulfanyl-propyl)-[1,3]dioxane
• CAS: 138092-01-0
• 化学式: C₁₁H₂₂O₂S
• 分子量: 218.36
• InChiKey: IIIMXHFQFSNSHM-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (2S,3R,4R)-4-Mercaptomethyl-2-methyl-hexane-1,3-diol 、 丙酮 在 对甲苯磺酸 作用下， 以 various solvent(s) 为溶剂， 生成 (4S,5R)-2,2,5-Trimethyl-4-((S)-1-methylsulfanyl-propyl)-[1,3]dioxane
  参考文献：
  名称：

  Stereocontrol in the Mukaiyama aldol addition to chiral .alpha.- and .beta.-thio-substituted aldehydes

  摘要：

  A series of racemic alpha-thio-, beta-thio-, and alpha-methyl-beta-thio-substituted aldehydes has been prepared, and their Lewis acid promoted aldol condensation with nonstereogenic and stereogenic silylketene acetals and silyl enolethers has been studied. With alpha-thio-substituted aldehydes, a high level of non-chelation-controlled diastereofacial selectivity can be easily achieved, while chelation control requires a strongly chelating catalyst and a small, aliphatic S-protecting group. Some examples of addition of stereogenic nucleophiles occurring with efficient diastereofacial syn simple stereoselection are also reported. The reactions of beta-thio-substituted aldehydes are less stereoselective, in particular when the stereocenter is in the beta-position. Models of stereoselection are presented to rationalize the results that were compared with those obtained in similar reactions with chiral alkoxy aldehydes.

  DOI：

  10.1021/jo00028a015