(R,S)-3-benzyloxy-4-hydroxy-Δ²-isoxazoline butyrate | 150884-61-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R,S)-3-benzyloxy-4-hydroxy-Δ²-isoxazoline butyrate
• 英文别名: Ulckxndalrkdgi-uhfffaoysa-；(3-phenylmethoxy-4,5-dihydro-1,2-oxazol-4-yl) butanoate
• CAS: 150884-61-0
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: ULCKXNDALRKDGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R,S)-3-benzyloxy-4-hydroxy-Δ²-isoxazoline butyrate 在 二苯基膦叠氮化物 、 水 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 4.75h， 生成 (S)-3-benzyloxy-4-acetylamino-Δ2-isoxazoline
  参考文献：
  名称：

  Chemoenzymatic synthesis of acetyl (R)-(+)- and (S)-(−)-cycloserine

  摘要：

  The two enantiomers of acetyl cycloserine 8, the immediate precursors of the chiral forms of cycloserine 1, were prepared in enantiomeric excess higher than 98% by means of lipase-catalyzed hydrolysis of 3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate (+/-)-5. Among the five lipases tested, lipase from Chromobacterium viscosum was by far the most selective catalyst. Since the enantiomeric ratio (E) of the reaction was higher than 100, the hydrolysis spontaneously stopped at 50% conversion to yield (R)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline [(R)-(+)-4] and (S)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate [(S)-(-)-5] in almost enantiomerically pure form. Intermediates (R)-(+)-4 and (S)-(-)-5 were transformed into the enantiomers of acetyl cycloserine through a four step sequence. This strategy constitutes a valid alternative to the previously reported procedures.

  DOI：

  10.1016/s0957-4166(00)80156-1
• 作为产物：
  描述：

  lithium benzyloxide 以 甲醇 、 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 (R,S)-3-benzyloxy-4-hydroxy-Δ²-isoxazoline butyrate
  参考文献：
  名称：

  Chemoenzymatic synthesis of acetyl (R)-(+)- and (S)-(−)-cycloserine

  摘要：

  The two enantiomers of acetyl cycloserine 8, the immediate precursors of the chiral forms of cycloserine 1, were prepared in enantiomeric excess higher than 98% by means of lipase-catalyzed hydrolysis of 3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate (+/-)-5. Among the five lipases tested, lipase from Chromobacterium viscosum was by far the most selective catalyst. Since the enantiomeric ratio (E) of the reaction was higher than 100, the hydrolysis spontaneously stopped at 50% conversion to yield (R)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline [(R)-(+)-4] and (S)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate [(S)-(-)-5] in almost enantiomerically pure form. Intermediates (R)-(+)-4 and (S)-(-)-5 were transformed into the enantiomers of acetyl cycloserine through a four step sequence. This strategy constitutes a valid alternative to the previously reported procedures.

  DOI：

  10.1016/s0957-4166(00)80156-1

文献信息

• Chemoenzymatic synthesis of acetyl (R)-(+)- and (S)-(−)-cycloserine
  作者：Marco de Amici、Carlo de Micheli、Francesca Cateni、Giacomo Carrea、Gianluca Ottolina

  DOI：10.1016/s0957-4166(00)80156-1

  日期：1993.5

  The two enantiomers of acetyl cycloserine 8, the immediate precursors of the chiral forms of cycloserine 1, were prepared in enantiomeric excess higher than 98% by means of lipase-catalyzed hydrolysis of 3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate (+/-)-5. Among the five lipases tested, lipase from Chromobacterium viscosum was by far the most selective catalyst. Since the enantiomeric ratio (E) of the reaction was higher than 100, the hydrolysis spontaneously stopped at 50% conversion to yield (R)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline [(R)-(+)-4] and (S)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate [(S)-(-)-5] in almost enantiomerically pure form. Intermediates (R)-(+)-4 and (S)-(-)-5 were transformed into the enantiomers of acetyl cycloserine through a four step sequence. This strategy constitutes a valid alternative to the previously reported procedures.