(3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[4-(methoxycarbonyl)-2-thiazolyl]isoxazolidine | 873920-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[4-(methoxycarbonyl)-2-thiazolyl]isoxazolidine
• CAS: 873920-45-7
• 化学式: C₂₀H₂₄N₂O₅S
• 分子量: 404.487
• InChiKey: RBEGRDZCSCCUHZ-GVDBMIGSSA-N

反应信息

• 作为反应物：
  描述：

  (3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[4-(methoxycarbonyl)-2-thiazolyl]isoxazolidine 在 sodium periodate 、 silica gel 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 4.33h， 生成 2-((3S,5R)-2-Benzyl-3-formyl-isoxazolidin-5-yl)-thiazole-4-carboxylic acid methyl ester
  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,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[(4RS)-4-(methoxycarbonyl)-2-thiazolin-2-yl]isoxazolidine 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 反应 12.0h， 以88%的产率得到(3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[4-(methoxycarbonyl)-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