((3R,5S)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl)methyl propionate | 1158823-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ((3R,5S)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl)methyl propionate
• CAS: 1158823-88-1
• 化学式: C₁₃H₁₉N₃O₅
• 分子量: 297.311
• InChiKey: YQMXYAPLJHXBQS-ZJUUUORDSA-N

物化性质

• 密度：
  1.257±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  93.63
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ((3R,5S)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl)methyl propionate 在 氨 、 水 作用下， 以 甲醇 为溶剂， 以99 mg的产率得到1-[(3R,5S)-3-(hydroxymethyl)-2-methylisoxazolidin-5-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Preparation of isoxazolidinyl nucleoside enantiomers by lipase-catalysed kinetic resolution

  摘要：

  An efficient biocatalytic procedure to obtain chiral N,O-nucleoside derivatives consisting of a lipase-catalysed resolution of the corresponding racemates in organic solvent has been developed. Enantioselective esterification of thymine and cytosine derivatives, (+/-)-9a and (+/-)-9b, has been Investigated by comparing the efficiency of different lipases and acyl donors. Since esterification of (+/-)-9a and (+/-)-9b, Occurred with low enantioselectivity (E <= 14) in the presence of the lipases considered, for preparative purposes we resorted, with Success, to a double sequential kinetic resolution, using Lipozyme IM as the best catalyst. This approach enables LIS to obtain all the enantiomers with ee >= 95%. The absolute configuration of the new chiral N-acetyl cytosine derivative 9b was established by circular dichroism spectroscopy. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.026
• 作为产物：
  描述：

  丙酸乙烯酯 、 1-[(3S,5R)-3-(hydroxymethyl)-2-methylisoxazolidin-5-yl]-5-methylpyrimidine-2,4(1H,3H)-dione 在 M_. miehei lipase 、 苯甲酸乙烯酯 、 氨 、 水 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 8.0h， 生成 ((3R,5S)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl)methyl propionate
  参考文献：
  名称：

  Preparation of isoxazolidinyl nucleoside enantiomers by lipase-catalysed kinetic resolution

  摘要：

  An efficient biocatalytic procedure to obtain chiral N,O-nucleoside derivatives consisting of a lipase-catalysed resolution of the corresponding racemates in organic solvent has been developed. Enantioselective esterification of thymine and cytosine derivatives, (+/-)-9a and (+/-)-9b, has been Investigated by comparing the efficiency of different lipases and acyl donors. Since esterification of (+/-)-9a and (+/-)-9b, Occurred with low enantioselectivity (E <= 14) in the presence of the lipases considered, for preparative purposes we resorted, with Success, to a double sequential kinetic resolution, using Lipozyme IM as the best catalyst. This approach enables LIS to obtain all the enantiomers with ee >= 95%. The absolute configuration of the new chiral N-acetyl cytosine derivative 9b was established by circular dichroism spectroscopy. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.026