(4S,5R)-5-((R)-(1,3-dithian-2-yl)(hydroxy)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide | 1018750-54-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-5-((R)-(1,3-dithian-2-yl)(hydroxy)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide
• 英文别名: (4S,5R)-5-[(R)-1,3-dithian-2-yl(hydroxy)methyl]-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide
• CAS: 1018750-54-3
• 化学式: C₁₃H₂₃NO₄S₂
• 分子量: 321.462
• InChiKey: FESAIVSWWIUNEN-BBBLOLIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-((R)-(1,3-dithian-2-yl)(hydroxy)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide 、 叔丁基二甲硅基三氟甲磺酸酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到(4S,5S)-5-((R)-(1,3-dithian-2-yl)(tert-butyldimethylsilyloxy)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide
  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,5R)-5-(1-oxo(1,3-dithian-2-yl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以97%的产率得到(4S,5R)-5-((R)-(1,3-dithian-2-yl)(hydroxy)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide
  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.