(3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[4-(ethoxycarbonyl)-2-thiazolyl]isoxazolidine | 873920-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[4-(ethoxycarbonyl)-2-thiazolyl]isoxazolidine
• CAS: 873920-52-6
• 化学式: C₂₁H₂₆N₂O₅S
• 分子量: 418.514
• InChiKey: ZPZVWQLMEKSIFN-OKZBNKHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  70.12
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[4-(ethoxycarbonyl)-2-thiazolyl]isoxazolidine 在 sodium tetrahydroborate 、 sodium periodate 、 氨 、 silica gel 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.33h， 生成 (3S,5S)-2-benzyl-3-(hydroxymethyl)-5-[4-(aminocarbonyl)-2-thiazolyl]isoxazolidine
  参考文献：
  名称：

  An efficient approach to enantiomeric isoxazolidinyl analogues of tiazofurin based on nitrone cycloadditions

  摘要：

  An efficient synthetic route to isoxazolidinyl analogues of tiazofurin has been developed. The strategy involves, as a key step, a 1,3-dipolar cycloaddition between acrylonitrile and chiral nonracemic nitrones. An opposite diastereofacial induction was observed when the chiral group was placed at either the carbon atom or the nitrogen one of the nitrone function. The 2-cyano isoxazolidines obtained were further converted into the enantiomeric target compounds by constructing the thiazole ring via condensation with L-cysteine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.004
• 作为产物：
  描述：

  (3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[(4RS)-4-(ethoxycarbonyl)-2-thiazolin-2-yl]isoxazolidine 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 反应 12.0h， 以92%的产率得到(3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[4-(ethoxycarbonyl)-2-thiazolyl]isoxazolidine
  参考文献：
  名称：

  An efficient approach to enantiomeric isoxazolidinyl analogues of tiazofurin based on nitrone cycloadditions

  摘要：

  An efficient synthetic route to isoxazolidinyl analogues of tiazofurin has been developed. The strategy involves, as a key step, a 1,3-dipolar cycloaddition between acrylonitrile and chiral nonracemic nitrones. An opposite diastereofacial induction was observed when the chiral group was placed at either the carbon atom or the nitrogen one of the nitrone function. The 2-cyano isoxazolidines obtained were further converted into the enantiomeric target compounds by constructing the thiazole ring via condensation with L-cysteine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.004