(+)-ethyl N,O-diacetyl-3-amino-2-hydroxypropionate | 137622-42-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-ethyl N,O-diacetyl-3-amino-2-hydroxypropionate
• CAS: 137622-42-5
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: QXNNUTGSGVJADY-QMMMGPOBSA-N

物化性质

• 沸点：
  375.2±32.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.38
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+)-ethyl N,O-diacetyl-3-amino-2-hydroxypropionate 在 盐酸 作用下， 反应 4.0h， 以96%的产率得到L-异丝氨酸
  参考文献：
  名称：

  A simple total synthesis of naturally occurring hydroxy-amino acids by enzymatic kinetic resolution

  摘要：

  Both optically pure enantiomers of GABOB and isoserine were obtained by enzymatic kinetic resolution of acetylated precursors in three or four steps. The key intermediates were cyanohydrins available from simple aldehydes. This procedure can be applied to other unusual hydroxy amino acids widely distributed in biologically important peptides.

  DOI：

  10.1016/s0957-4166(00)80128-7
• 作为产物：
  描述：

  (+/-)-ethyl 2-cyano-2-hydroxyacetate 在 吡啶 、 硼烷四氢呋喃络合物 、 nickel dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 (+)-ethyl N,O-diacetyl-3-amino-2-hydroxypropionate
  参考文献：
  名称：

  A simple total synthesis of naturally occurring hydroxy-amino acids by enzymatic kinetic resolution

  摘要：

  Both optically pure enantiomers of GABOB and isoserine were obtained by enzymatic kinetic resolution of acetylated precursors in three or four steps. The key intermediates were cyanohydrins available from simple aldehydes. This procedure can be applied to other unusual hydroxy amino acids widely distributed in biologically important peptides.

  DOI：

  10.1016/s0957-4166(00)80128-7

文献信息

• A simple total synthesis of (S)-isoserine
  作者：Yang Lu、Christine Miet、Nicole Kunesch、Jacques E. Poisson

  DOI：10.1016/s0957-4166(00)82197-7

  日期：1991.1

  Kinetic enzymatic resolution by Candida cylindracea lipase of racemic isoserine diacetate prepared from the cyanohydrin of glyoxylate provided (S)-isoserine in good yeild and high optical purity.