methyl 4-<(tert-butyloxycarbonyl)amino>-5-hydroxypentanoate | 146398-08-5

• 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 4-<(tert-butyloxycarbonyl)amino>-5-hydroxypentanoate
• 英文别名: methyl (4R)-4-(tert-butoxycarbonylamino)-5-hydroxypentanoate；Methyl (4R)-4-[(tert-butoxycarbonyl)amino]-5-hydroxypentanoate；methyl (4R)-5-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 146398-08-5
• 化学式: C₁₁H₂₁NO₅
• 分子量: 247.291
• InChiKey: SRVJJSKMYILGAM-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-<(tert-butyloxycarbonyl)amino>-5-hydroxypentanoate 在 吡啶 、 sodium hydroxide 、 sodium iodide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 4.17h， 生成 Boc-γ-L-二高亮氨酸
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure β- and γ-Amino Acids from Aspartic and Glutamic Acid Derivatives

  摘要：

  描述了一种高效合成手性纯的β-和γ-氨基酸的方法，该方法从市售的谷氨酸和天冬氨酸衍生物出发。首先将氨基酸的α位羧基转化为良好的离去基团，然后与有机铜试剂反应，生成β-和γ-氨基酸酯。经过脱保护步骤后，以良好的总产率获得β-和γ-氨基酸。

  DOI：

  10.1055/s-1992-26315
• 作为产物：
  描述：

  D-谷氨酸-5-甲酯 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 8.5h， 生成 methyl 4-<(tert-butyloxycarbonyl)amino>-5-hydroxypentanoate
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure β- and γ-Amino Acids from Aspartic and Glutamic Acid Derivatives

  摘要：

  描述了一种高效合成手性纯的β-和γ-氨基酸的方法，该方法从市售的谷氨酸和天冬氨酸衍生物出发。首先将氨基酸的α位羧基转化为良好的离去基团，然后与有机铜试剂反应，生成β-和γ-氨基酸酯。经过脱保护步骤后，以良好的总产率获得β-和γ-氨基酸。

  DOI：

  10.1055/s-1992-26315

文献信息

• [EN] AMINOCYCLOHEXANES AND AMINOTETRAHYDROPYRANS AND RELATED COMPOUNDS AS GAMMA-SECRETASE MODULATORS<br/>[FR] AMINOCYCLOHEXANES ET AMINOTÉTRAHYDROPYRANES ET COMPOSÉS ASSOCIÉS COMME MODULATEURS DE GAMMA-SÉCRÉTASE
  申请人：PFIZER

  公开号：WO2011092611A1

  公开（公告）日：2011-08-04

  Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  本发明揭示了化合物及其在规范中定义的结构为式（I）的药学上可接受的盐。同时还公开了相应的药物组合物、治疗方法、合成方法和中间体。
• Aminocyclohexanes and Aminotetrahydropyrans and Related Compounds As Gamma-Secretase Modulators
  申请人：Am Ende Christopher William

  公开号：US20120295923A1

  公开（公告）日：2012-11-22

  Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  本发明揭示了化合物及其药学上可接受的盐，其中所述化合物具有规范中定义的I式结构。同时还揭示了相应的药物组合物、治疗方法、合成方法和中间体。
• Structure−Activity Relationship of 2-Oxoamide Inhibition of Group IVA Cytosolic Phospholipase A₂ and Group V Secreted Phospholipase A₂
  作者：David A. Six、Efrosini Barbayianni、Vassilios Loukas、Violetta Constantinou-Kokotou、Dimitra Hadjipavlou-Litina、Daren Stephens、Alan C. Wong、Victoria Magrioti、Panagiota Moutevelis-Minakakis、Sharon F. Baker、Edward A. Dennis、George Kokotos

  DOI：10.1021/jm0613673

  日期：2007.8.1

  The Group IVA cytosolic phospholipase A(2) (GIVA cPLA(2)) is a key provider of substrates for the production of eicosanoids and platelet-activating factor. We explored the structure-activity relationship of 2-oxoamide-based compounds and GIVA cPLA(2) inhibition. The most potent inhibitors are derived from delta- and gamma-amino acid-based 2-oxoamides. The optimal side-chain moiety is a short nonpolar aliphatic chain. All of the newly developed 2-oxoamides as well as those previously described have now been tested with the human Group V secreted PLA(2) (GV sPLA(2)) and the human Group VIA calcium-independent PLA(2) (GVIA iPLA(2)). Only one 2-oxoamide compound had appreciable inhibition of GV sPLA(2), and none of the potent GIVA cPLA(2) inhibitors inhibited either GV sPLA(2) or GVIA iPLA(2). Two of these specific GIVA cPLA(2) inhibitors were also found to have potent therapeutic effects in animal models of pain and inflammation at dosages well below the control nonsteroidal anti-inflammatory drugs.
• WO2024061853A1
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of Enantiomerically Pure β- and γ-Amino Acids from Aspartic and Glutamic Acid Derivatives
  作者：A. El Marini、M. L. Roumestant、Ph. Viallefont、D. Razafindramboa、M. Bonato、M. Follet

  DOI：10.1055/s-1992-26315

  日期：——

  An efficient synthesis of enantiomerically pure β- and γ-amino acids starting from commercially available aspartic and glutamic acid derivatives is described. The acid function, α to the amino group, is first transformed to a good leaving group and the product reacted with organocuprates to yield β-and γ-amino esters. After deprotection β- and γ-amino acids are obtained in good overall yields.

  描述了一种高效合成手性纯的β-和γ-氨基酸的方法，该方法从市售的谷氨酸和天冬氨酸衍生物出发。首先将氨基酸的α位羧基转化为良好的离去基团，然后与有机铜试剂反应，生成β-和γ-氨基酸酯。经过脱保护步骤后，以良好的总产率获得β-和γ-氨基酸。