(S)-2-氨基-3-(4-(2-叔丁氧基-2-氧代乙基)苯基)丙酸 | 222842-90-2

• 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: (S)-2-氨基-3-(4-(2-叔丁氧基-2-氧代乙基)苯基)丙酸
• 英文名称: 4-(tert-butoxycarbonylmethyl)-L-phenylalanine
• 英文别名: (S)-2-Amino-3-(4-(2-tert-butoxy-2-oxoethyl)phenyl)propanoic acid；(2S)-2-amino-3-[4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]phenyl]propanoic acid
• CAS: 222842-90-2
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: NGMNYXQCCBKDET-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 (S)-2-氨基-3-(4-(2-叔丁氧基-2-氧代乙基)苯基)丙酸 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以93%的产率得到N-Fmoc-4-(tert-butoxycarbonylmethyl)-L-phenylalanine
  参考文献：
  名称：

  Synthesis of Fmoc-protected 4-carboxydifluoromethyl-L-phenylalanine: A phosphotyrosyl mimetic of potential use for signal transduction studies

  摘要：

  4-(Carboxymethyl)phenylalanine (2) and its alpha,alpha-difluoro homologue 4-(carboxydifluoromethyl)-phenylalanine (3) have been described as phosphotyrosyl mimetics. Herein we report the synthesis of N-Fmoc 4-(0-tert-butyl carboxymethyl)-phenylalanine (4) and N-Fmoc 4-(0-tert-butyl carboxydifluoromethyl)phenylalanine (5) in high enantiomeric purity. These analogues bear orthogonal protection suitable for the preparation of inhibitors directed against a variety of signal transduction pathways, including SH2 and PTP domains and protein-tyrosine phosphatases. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(99)00076-9
• 作为产物：
  描述：

  对叔丁基苯乙酸甲酯 在 钯 N-溴代丁二酰亚胺(NBS) 、 (PhCOO)2O 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 六甲基磷酰三胺 为溶剂， 反应 23.5h， 生成 (S)-2-氨基-3-(4-(2-叔丁氧基-2-氧代乙基)苯基)丙酸
  参考文献：
  名称：

  Synthesis of Fmoc-protected 4-carboxydifluoromethyl-L-phenylalanine: A phosphotyrosyl mimetic of potential use for signal transduction studies

  摘要：

  4-(Carboxymethyl)phenylalanine (2) and its alpha,alpha-difluoro homologue 4-(carboxydifluoromethyl)-phenylalanine (3) have been described as phosphotyrosyl mimetics. Herein we report the synthesis of N-Fmoc 4-(0-tert-butyl carboxymethyl)-phenylalanine (4) and N-Fmoc 4-(0-tert-butyl carboxydifluoromethyl)phenylalanine (5) in high enantiomeric purity. These analogues bear orthogonal protection suitable for the preparation of inhibitors directed against a variety of signal transduction pathways, including SH2 and PTP domains and protein-tyrosine phosphatases. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(99)00076-9

文献信息

• RAPAFUCIN DERIVATIVE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：The Johns Hopkins University

  公开号：US20210094933A1

  公开（公告）日：2021-04-01

  The present disclosure provides macrocyclic compounds inspired by the immunophilin ligand family of natural products FK506 and rapamycin. The generation of a Rapafucin library of macrocyles that contain FK506 and rapamycin binding domains should have great potential as new leads for developing drugs to be used for treating diseases.

  本公开提供了受免疫蛋白配体家族FK506和雷帕霉素天然产物启发的大环化合物。生成包含FK506和雷帕霉素结合结构域的Rapafucin大环化合物库，应具有作为治疗疾病新药的潜力。
• Rapafucin derivative compounds and methods of use thereof
  申请人：The Johns Hopkins University

  公开号：US11066416B2

  公开（公告）日：2021-07-20

  The present disclosure provides macrocyclic compounds inspired by the immunophilin ligand family of natural products FK506 and rapamycin. The generation of a Rapafucin library of macrocyles that contain FK506 and rapamycin binding domains should have great potential as new leads for developing drugs to be used for treating diseases.

  本公开提供了受天然产物 FK506 和雷帕霉素的免疫嗜蛋白配体家族启发的大环化合物。由含有 FK506 和雷帕霉素结合结构域的大环化合物组成的雷帕霉素库，作为开发用于治疗疾病的药物的新线索，具有巨大的潜力。
• PYRIDONES AS SRC FAMILY SH2 DOMAIN INHIBITORS
  申请人：Boehringer Ingelheim Pharmaceuticals Inc.

  公开号：EP1045836B1

  公开（公告）日：2008-03-05
• [EN] RAPAFUCIN DERIVATIVE COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS DÉRIVÉS DE LA RAPAFUCINE ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2021067439A1

  公开（公告）日：2021-04-08

  The present disclosure provides macrocyclic compounds inspired by the immunophilin ligand family of natural products FK506 and rapamycin. The generation of a Rapafucin library of macrocyles that contain FK506 and rapamycin binding domains should have great potential as new leads for developing drugs to be used for treating diseases.
• Synthesis of Fmoc-protected 4-carboxydifluoromethyl-L-phenylalanine: A phosphotyrosyl mimetic of potential use for signal transduction studies
  作者：Zhu-Jun Yao、Yang Gao、Johannes H Voigt、Harry Ford、Terrence R Burke

  DOI：10.1016/s0040-4020(99)00076-9

  日期：1999.3

  4-(Carboxymethyl)phenylalanine (2) and its alpha,alpha-difluoro homologue 4-(carboxydifluoromethyl)-phenylalanine (3) have been described as phosphotyrosyl mimetics. Herein we report the synthesis of N-Fmoc 4-(0-tert-butyl carboxymethyl)-phenylalanine (4) and N-Fmoc 4-(0-tert-butyl carboxydifluoromethyl)phenylalanine (5) in high enantiomeric purity. These analogues bear orthogonal protection suitable for the preparation of inhibitors directed against a variety of signal transduction pathways, including SH2 and PTP domains and protein-tyrosine phosphatases. Published by Elsevier Science Ltd.