(2S,4S)-N-Boc-4-hydroxypiperidine-2-carboxylic acid benzylamine salt

• 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: (2S,4S)-N-Boc-4-hydroxypiperidine-2-carboxylic acid benzylamine salt
• 英文别名: benzylazanium;(2S,4S)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-2-carboxylate
• 化学式: C₇H₉N*C₁₁H₁₉NO₅
• 分子量: 352.431
• InChiKey: QMLALKYUTWPCAI-WSZWBAFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4S)-N-Boc-4-hydroxypiperidine-2-carboxylic acid benzylamine salt 在 SCX resin 作用下， 以 甲醇 为溶剂， 生成 (2S,4S)-N-Boc-4-hydroxypiperidine-2-carboxylic acid
  参考文献：
  名称：

  WO2006/90163

  摘要：

  公开号：
• 作为产物：
  描述：

  4-羟基-2-哌啶甲酸 、 二碳酸二叔丁酯 在 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 生成 (2S,4S)-N-Boc-4-hydroxypiperidine-2-carboxylic acid benzylamine salt
  参考文献：
  名称：

  Chemoenzymatic Synthesis of the Four Diastereoisomers of 4-Hydroxypipecolic Acid from N-Acetyl-(R,S)-allylglycine:  Chiral Scaffolds for Drug Discovery

  摘要：

  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.

  DOI：

  10.1021/op020017x

文献信息

• Solid-Phase Synthesis of Dihydrovirginiamycin S1, a Streptogramin B Antibiotic
  作者：Alex Shaginian、Marissa C. Rosen、Brock F. Binkowski、Peter J. Belshaw

  DOI：10.1002/chem.200400267

  日期：2004.9.6

  solid-phase synthesis of dihydrovirginiamycin S(1), a member of the streptogramin B family of antibiotics, which are nonribosomal-peptide natural products produced by Streptomyces. These compounds, along with the synergistic group A components, are "last line of defense" antimicrobial agents for the treatment of life-threatening infections such as vancomycin-resistant enterococci. The synthesis features

  我们描述了二氢维吉尼亚霉素S（1）的第一个固相合成，这是链霉菌素B族抗生素的一种，这是链霉菌产生的非核糖体肽天然产物。这些化合物与协同作用的A组组分一起，是用于治疗威胁生命的感染（如耐万古霉素的肠球菌）的“最后防线”抗菌剂。该合成具有树脂上的环化作用，旨在允许在位置1'，1、2、3、4和6处产生多样化的链霉菌素B类似物。通过明智地选择脱保护条件，偶联条件，解决了对酸和碱的敏感性以及差向异构和重排的问题，和综合策略。这项工作应该能够更好地了解链蛋白B化合物中的结构-活性关系，可能绕过已知耐药机制的类似物的鉴定，以及可能具有新生物活性的类似物的鉴定。
• INHIBITORS OF SPHINGOSINE KINASE 1
  申请人：Xiang Yibin

  公开号：US20110275673A1

  公开（公告）日：2011-11-10

  The invention relates to compounds of Formula (I). Compounds of the present invention are inhibitors of sphingosine kinase 3, and are useful in the treatment of various disorders and conditions, such as inflammatory disorders.

  本发明涉及公式（I）的化合物。本发明的化合物是鞘氨醇激酶3的抑制剂，并且在治疗各种疾病和病况，例如炎症性疾病方面非常有用。
• WO2006/90163
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.