(R)-((4R,5S)-5-((R)-(1,3-dithian-2-yl)(tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methanol | 1018750-86-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-((4R,5S)-5-((R)-(1,3-dithian-2-yl)(tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methanol
• 英文别名: (R)-[(4R,5S)-5-[(R)-[tert-butyl(dimethyl)silyl]oxy-(1,3-dithian-2-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethanol
• CAS: 1018750-86-1
• 化学式: C₂₃H₃₈O₄S₂Si
• 分子量: 470.77
• InChiKey: DCBDIEGGZFQEKE-YSTOQKLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-((4R,5S)-5-((R)-(1,3-dithian-2-yl)(tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methanol 、 氯甲基甲基醚 在 4-二甲氨基吡啶 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以97%的产率得到((R)-(1,3-dithian-2-yl)((4S,5R)-5-((R)-(methoxymethoxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)(tert-butyl)dimethylsilane
  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：

  在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以94%的产率得到(R)-((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

文献信息

• Stereoselective Total Synthesis of (+)-Cardiobutanolide
  作者：Kavirayani R. Prasad、Shivajirao L. Gholap

  DOI：10.1021/jo7025614

  日期：2008.4.1

  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.