methyl (2S,3R)-3-cyclohexyl-3-hydroxy-2-[[(1S)-2-hydroxy-1-phenylethyl]amino]propanoate | 208932-24-5

• 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: methyl (2S,3R)-3-cyclohexyl-3-hydroxy-2-[[(1S)-2-hydroxy-1-phenylethyl]amino]propanoate
• CAS: 208932-24-5
• 化学式: C₁₈H₂₇NO₄
• 分子量: 321.417
• InChiKey: PTHOGVSDORLUOL-IXDOHACOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R)-3-cyclohexyl-3-hydroxy-2-[[(1S)-2-hydroxy-1-phenylethyl]amino]propanoate 在 palladium dihydroxide 氢气 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以37 mg的产率得到(2S,3R)-β-cyclohexylserine
  参考文献：
  名称：

  Application of enantiopure templated azomethine ylids to β-hydroxy-α-amino acid synthesis

  摘要：

  Chiral stabilised azomethine ylids derived from the reaction of (5S)-5-phenylmorpholin-2-one (1) with aldehydes undergo efficient and highly diastereocontrolled cycloaddition with a second molecule of aldehyde to furnish products (2) which may be converted into enantiomerically pure three (2S,3R) beta-hydroxy-alpha-amino acids (3) in excellent yield, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00302-0
• 作为产物：
  描述：

  (5S)-3,4,5,6-四氢-5-苯基-4(H)-1,4-恶嗪-2-酮 在 盐酸 作用下， 以 水 、 甲苯 为溶剂， 反应 48.0h， 生成 methyl (2S,3R)-3-cyclohexyl-3-hydroxy-2-[[(1S)-2-hydroxy-1-phenylethyl]amino]propanoate
  参考文献：
  名称：

  Application of enantiopure templated azomethine ylids to β-hydroxy-α-amino acid synthesis

  摘要：

  Chiral stabilised azomethine ylids derived from the reaction of (5S)-5-phenylmorpholin-2-one (1) with aldehydes undergo efficient and highly diastereocontrolled cycloaddition with a second molecule of aldehyde to furnish products (2) which may be converted into enantiomerically pure three (2S,3R) beta-hydroxy-alpha-amino acids (3) in excellent yield, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00302-0

文献信息

• Application of enantiopure templated azomethine ylids to β-hydroxy-α-amino acid synthesis
  作者：David Alker、Giles Hamblett、Laurence M. Harwood、Sarah M. Robertson、David J. Watkin、C. Eleri Williams

  DOI：10.1016/s0040-4020(98)00302-0

  日期：1998.5

  Chiral stabilised azomethine ylids derived from the reaction of (5S)-5-phenylmorpholin-2-one (1) with aldehydes undergo efficient and highly diastereocontrolled cycloaddition with a second molecule of aldehyde to furnish products (2) which may be converted into enantiomerically pure three (2S,3R) beta-hydroxy-alpha-amino acids (3) in excellent yield, (C) 1998 Elsevier Science Ltd. All rights reserved.