(2S,4S)-1-苯甲基2-甲基4-羟基哌啶-1,2-二甲酸基酯 | 403503-43-5

• 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
• 中文名称: (2S,4S)-1-苯甲基2-甲基4-羟基哌啶-1,2-二甲酸基酯
• 英文名称: methyl 1-benzyloxycarbonyl-trans-4-hydroxy-(S)-pipecolate
• 英文别名: (2S,4S)-4-hydroxypipecolic acid methyl ester；(2S,4S)-1-Benzyl 2-methyl 4-hydroxypiperidine-1,2-dicarboxylate；1-O-benzyl 2-O-methyl (2S,4S)-4-hydroxypiperidine-1,2-dicarboxylate
• CAS: 403503-43-5
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: UZYUNWAMEQIRQH-STQMWFEESA-N

物化性质

• 沸点：
  436.1±45.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4S)-1-苯甲基2-甲基4-羟基哌啶-1,2-二甲酸基酯 在 palladium dihydroxide 盐酸 、 氢气 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Stereoselective syntheses of 4-fluoro- and 4,4-difluoropipecolic acids

  摘要：

  Stereoselective syntheses of 4-fluoro- and 4,4-difluoropipecolic acids starting from Z-protected 4-hydroxy- and 4-oxopipecolates via fluorodehydroxylation and fluorodeoxygenation are described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01660-4
• 作为产物：
  描述：

  N-CBZ--L-烯丙基甘氨酸 在 氯化亚砜 、 lipase AY₃₀ from Candida rugosa 作用下， 生成 (2S,4S)-1-苯甲基2-甲基4-羟基哌啶-1,2-二甲酸基酯
  参考文献：
  名称：

  水解酶在合成环状氨基酸中的用途

  摘要：

  描述了具有所有必要结构特征以使其成为用于药物化学的理想支架的几种环状氨基酸的合成。每个合成过程中的关键步骤是使用水解酶来定义手性中心。为了将这些结构单元详细化为更复杂的分子，使用了结晶和不对称氢化来定义进一步的立体中心。

  DOI：

  10.1016/j.tet.2003.10.116

文献信息

• Novel constrained CCK-B dipeptoid antagonists derived from pipecolic acid
  作者：Bruno Bellier、Sophie Da Nascimento、Hervé Meudal、Edith Gincel、Bernard P. Roques、Christiane Garbay

  DOI：10.1016/s0960-894x(98)00231-5

  日期：1998.6

  A new series of 4-substituted pipecolic acid derivatives was prepared and incorporated into dipeptoids. The resulting products behave as moderately potent CCK-B antagonists but their constrained structure and its comparison with structurally related compounds yield valuable information about the conformational requirements for optimal recognition of the CCK-B receptor by antagonists. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Chemoenzymatic Synthesis of the Four Diastereoisomers of 4-Hydroxypipecolic Acid from <i>N</i>-Acetyl-(<i>R</i>,<i>S</i>)-allylglycine:  Chiral Scaffolds for Drug Discovery
  作者：Richard C. Lloyd、Mark E. B. Smith、Dean Brick、Stephen J. C. Taylor、David A. Chaplin、Raymond McCague

  DOI：10.1021/op020017x

  日期：2002.11.1

  All four diastereoisomers of 4-hydroxypipecolic acid were prepared in a form conveniently protected for drug discovery applications with the use of industrially scaleable methodology. Resolution of the racemic starting material using proprietary acylases followed by an acyliminium ion cyclisation gave diastereomeric mixtures of 4-formyloxypipecolic acid, which were differentiated using an enzyme-catalysed hydrolysis. The products were separated, by partition, and by following a sequence of straightforward chemical steps, the individual stereoisomers of the protected 4-hydroxypipecolates were crystallized to optical purity in 100 g quantities.
• Use of hydrolases for the synthesis of cyclic amino acids
  作者：Richard C Lloyd、Michael C Lloyd、Mark E.B Smith、Karen E Holt、Jonathan P Swift、Philip A Keene、Stephen J.C Taylor、Raymond McCague

  DOI：10.1016/j.tet.2003.10.116

  日期：2004.1

  The synthesis of several cyclic amino acids that have all the necessary structural features to make them ideal scaffolds for use in medicinal chemistry is described. A key step in each synthesis is the use of hydrolase enzymes to define a chiral centre. In order to elaborate these building blocks into more complex molecules, crystallization and asymmetric hydrogenation were used to define further stereocentres

  描述了具有所有必要结构特征以使其成为用于药物化学的理想支架的几种环状氨基酸的合成。每个合成过程中的关键步骤是使用水解酶来定义手性中心。为了将这些结构单元详细化为更复杂的分子，使用了结晶和不对称氢化来定义进一步的立体中心。
• Stereoselective syntheses of 4-fluoro- and 4,4-difluoropipecolic acids
  作者：Alexander S Golubev、Hartmut Schedel、Gabor Radics、Joachim Sieler、Klaus Burger

  DOI：10.1016/s0040-4039(01)01660-4

  日期：2001.11

  Stereoselective syntheses of 4-fluoro- and 4,4-difluoropipecolic acids starting from Z-protected 4-hydroxy- and 4-oxopipecolates via fluorodehydroxylation and fluorodeoxygenation are described. (C) 2001 Elsevier Science Ltd. All rights reserved.