(2S,5S)-N-[(benzyloxy)carbonyl]-5-hydroxy-2-piperidinecarboxylic acid | 917507-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,5S)-N-[(benzyloxy)carbonyl]-5-hydroxy-2-piperidinecarboxylic acid
• 英文别名: N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid；(2S,5S)-1-((Benzyloxy)carbonyl)-5-hydroxypiperidine-2-carboxylic acid；(2S,5S)-5-hydroxy-1-phenylmethoxycarbonylpiperidine-2-carboxylic acid
• CAS: 917507-80-3
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: CFRMMWFGNLWFMK-RYUDHWBXSA-N

物化性质

• 熔点：
  131-132 °C
• 沸点：
  495.6±45.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5S)-N-[(benzyloxy)carbonyl]-5-hydroxy-2-piperidinecarboxylic acid 在 palladium on activated charcoal 氢气 作用下， 生成 (2S,5S)-5-羟基哌啶-2-甲酸
  参考文献：
  名称：

  An efficient route to the α-methyl ester ofL-glutamic acid, and its conversion into cis-5-hydroxy-L-pipecolic acid

  摘要：

  The treatment of the N-benzyloxycarbonyl alpha-methyl esters of L-glutamine or L-asparagine with tert-butyl nitrite in refluxing acetonitrile results-in selective hydrolysis of the amide group, giving optically pure Z-Glu-OMe (74%) or Z-Asp-OMe (88%); these are versatile chiral building blocks, and an efficient synthesis of cis-5-hydroxy-L pipecolic acid from Z-Glu-OMe is described.

  DOI：

  10.1039/cc9960000349
• 作为产物：
  描述：

  Z-L-GluOMe 在 dirhodium tetraacetate sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 0.5h， 生成 (2S,5S)-N-[(benzyloxy)carbonyl]-5-hydroxy-2-piperidinecarboxylic acid
  参考文献：
  名称：

  An efficient route to the α-methyl ester ofL-glutamic acid, and its conversion into cis-5-hydroxy-L-pipecolic acid

  摘要：

  The treatment of the N-benzyloxycarbonyl alpha-methyl esters of L-glutamine or L-asparagine with tert-butyl nitrite in refluxing acetonitrile results-in selective hydrolysis of the amide group, giving optically pure Z-Glu-OMe (74%) or Z-Asp-OMe (88%); these are versatile chiral building blocks, and an efficient synthesis of cis-5-hydroxy-L pipecolic acid from Z-Glu-OMe is described.

  DOI：

  10.1039/cc9960000349

文献信息

• Method for Producing cis-5-hydroxy-2-piperidinecarboxylic Acid Derivative, and Method for Purifying cis-5-hydroxy-2-piperidinecarboxylic Acid
  申请人：API CORPORATION

  公开号：US20150239906A1

  公开（公告）日：2015-08-27

  The present invention aims to provide a method for purifying cis-5-hydroxy-2-piperidinecarboxylic acid with high purity, and a method for producing its derivative. The present invention provides a method for producing a cis-5-hydroxy-2-piperidinecarboxylic acid derivative, which method comprises a step of converting cis-5-hydroxy-2-piperidinecarboxylic acid into a compound(s) of Formula (1) and/or Formula (2) (wherein R 1 represents a protective group for an amino group, and R2 represents a C 1 -C 6 alkyl group), and a method for purifying cis-5-hydroxy-2-piperidinecarboxylic acid.

  本发明旨在提供一种高纯度纯化顺式-5-羟基-2-哌啶羧酸的方法，以及其衍生物的生产方法。本发明提供了一种生产顺式-5-羟基-2-哌啶羧酸衍生物的方法，该方法包括将顺式-5-羟基-2-哌啶羧酸转化为式（1）和/或式（2）化合物的步骤（其中R1代表氨基的保护基，R2代表C1-C6烷基），以及一种纯化顺式-5-羟基-2-哌啶羧酸的方法。
• Diastereoselective synthesis of (2S,5S)- and (2S,5R)-N-benzyloxycarbonyl-5-hydroxypipecolic acids from trans-4-hydroxy-l-proline
  作者：Jae-Chul Jung、Mitchell A. Avery

  DOI：10.1016/j.tetasy.2006.07.035

  日期：2006.10

  An efficient diastereo selective synthesis of cis- and trans-5-hydroxy-(2S)-N-benzyloxycarbonyl pipecolic acids, starting from trans-4-hydrOXY-L-proline is described. The key synthetic strategies involve the regioisomeric ring expansion of keto ester 8 and diastereoselective reduction of ketone 11 in high selectivity and yield. (c) 2006 Elsevier Ltd. All rights reserved.
• METHOD FOR PRODUCING cis-5-HYDROXY-2-PIPERIDINECARBOXYLIC ACID DERIVATIVE, AND METHOD FOR PURIFYING cis-5-HYDROXY-2-PIPERIDINECARBOXYLIC ACID
  申请人：API Corporation

  公开号：EP2889288B1

  公开（公告）日：2018-07-25
• JP2015/40200
  申请人：——

  公开号：——

  公开（公告）日：——
• Chiral synthesis of 5-hydroxy-(L)-pipecolic acids from (L)-glutamic acid
  作者：Patrick D Bailey、Justin S Bryans

  DOI：10.1016/s0040-4039(00)86719-2

  日期：——