((4S,5S)-5-((R)-(1,3-dithian-2-yl)(tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methanone | 1018750-70-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((4S,5S)-5-((R)-(1,3-dithian-2-yl)(tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methanone
• CAS: 1018750-70-3
• 化学式: C₂₃H₃₆O₄S₂Si
• 分子量: 468.754
• InChiKey: BZTQJGGSVLFLAR-HSALFYBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((4S,5S)-5-((R)-(1,3-dithian-2-yl)(tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methanone 在 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以88%的产率得到(S)-((4R,5S)-5-((R)-(1,3-dithian-2-yl)(tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methanol
  参考文献：
  名称：

  Stereoselective Total Synthesis of (+)-Cardiobutanolide

  摘要：

  Stereoselective synthesis of styryllactone (+)-cardiobutanolide was accomplished in good overall yield from D-(-)-tartaric acid. Key features of the synthesis include the elaboration of a gamma-hydroxy butyramide obtained from the dimethylarnide of tartaric acid, involving a combination of the addition of 1,3-dithian-2-yllithium and stereoselective reduction.

  DOI：

  10.1021/jo7025614
• 作为产物：
  描述：

  (4S,5S)-5-((R)-(1,3-dithian-2-yl)(tert-butyldimethylsilyloxy)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide 、 phenylmagnesium bromide 以 四氢呋喃 为溶剂， 反应 0.5h， 以96%的产率得到((4S,5S)-5-((R)-(1,3-dithian-2-yl)(tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methanone
  参考文献：
  名称：

  Stereoselective Total Synthesis of (+)-Cardiobutanolide

  摘要：

  Stereoselective synthesis of styryllactone (+)-cardiobutanolide was accomplished in good overall yield from D-(-)-tartaric acid. Key features of the synthesis include the elaboration of a gamma-hydroxy butyramide obtained from the dimethylarnide of tartaric acid, involving a combination of the addition of 1,3-dithian-2-yllithium and stereoselective reduction.

  DOI：

  10.1021/jo7025614