(S)-N^α-tert-butoxycarbonyl-(m-benzyloxy)phenylalanine methyl ester | 447461-03-2

• 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
• 英文名称: (S)-N^α-tert-butoxycarbonyl-(m-benzyloxy)phenylalanine methyl ester
• 英文别名: methyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-3-[(phenylmethyl)oxy]-L-phenylalaninate；(S)-methyl-3-(3-(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate；(S)-3-(3-benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester；(S)-3-(3-benzyloxyphenyl)-2-tert-butoxycarbonylaminopropionic acid methyl ester；methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(3-phenylmethoxyphenyl)propanoate
• CAS: 447461-03-2
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: BVTBTSTTXPCVFJ-IBGZPJMESA-N

物化性质

• 沸点：
  529.8±50.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-N^α-tert-butoxycarbonyl-(m-benzyloxy)phenylalanine methyl ester 在 lithium hydroxide monohydrate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 18.17h， 生成 (S)-3-(3-(benzyloxy)phenyl)-2-((S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)propanoic acid
  参考文献：
  名称：

  Synthesis of the Southern Tripeptide (C₁–N₁₂) of Sanglifehrins Using Asymmetric Organocatalysis

  摘要：

  The tripeptide southern region of the novel cyclophilin binding natural product macrolides, namely sanglifehrins, is synthesized involving asymmetric organocatalysis as chirality-inducing step. List's asymmetric alpha-amination was used in the synthesis of the m-hydroxyphenylalanine part, whereas alpha-hydrazination was used for the piperazic ester part.

  DOI：

  10.1080/00397911.2014.947653
• 作为产物：
  描述：

  methyl (S)-2-amino-3-(3-hydroxyphenyl)propanoate 在 碳酸氢钠 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 20.0h， 生成 (S)-N^α-tert-butoxycarbonyl-(m-benzyloxy)phenylalanine methyl ester
  参考文献：
  名称：

  Synthesis of the Southern Tripeptide (C₁–N₁₂) of Sanglifehrins Using Asymmetric Organocatalysis

  摘要：

  The tripeptide southern region of the novel cyclophilin binding natural product macrolides, namely sanglifehrins, is synthesized involving asymmetric organocatalysis as chirality-inducing step. List's asymmetric alpha-amination was used in the synthesis of the m-hydroxyphenylalanine part, whereas alpha-hydrazination was used for the piperazic ester part.

  DOI：

  10.1080/00397911.2014.947653

文献信息

• Macrocyclic Compounds Useful as Bace Inhibitors
  申请人：Betschart Claudia

  公开号：US20080132477A1

  公开（公告）日：2008-06-05

  The invention relates to novel macrocyclic compounds of the formula (I), in which all of the variables are as defined in the specification, the number of ring atoms included in the macrocyclic ring being 14, 15, 16 or 17, in free base form or in acid addition salt form, to their preparation, to their use as medicaments and to medicaments comprising them.

  本发明涉及具有公式(I)的新型大环化合物，其中所有变量如说明书中所定义，大环环中包含的环原子数为14、15、16或17，以自由碱形式或酸加成盐形式存在，以及它们的制备方法、作为药物的使用以及包含它们的药物。
• Practical, asymmetric synthesis of aromatic-substituted bulky and hydrophobic tryptophan and phenylalanine derivatives
  作者：Wei Wang、Chiyi Xiong、Junyi Zhang、Victor J Hruby

  DOI：10.1016/s0040-4020(02)00162-x

  日期：2002.4

  Burk's DuPHOS-based Rh (I) catalysts generated high enantiomerically pure α-amino acid derivatives, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford these aromatic substituted amino acids in high yields and high enantioselectivity. The method can allow for the preparation of such amino acids in large scales for extensive structure–activity studies.

  芳香环取代的色氨酸和苯丙氨酸可以提供有价值的工具，以开发具有特定结构特征的强效和选择性肽配体，此外还可以提供一个大的亲脂性表面来与受体结合并穿越膜屏障。已经开发了合成这些新氨基酸的有效方法。在该方法中，使用Burk基于DuPHOS的Rh（I）催化剂进行α-酰胺的不对称氢化生成高对映体纯的α-氨基酸衍生物，随后将其与硼酸衍生物进行Suzuki交叉偶联，从而以高收率获得这些芳族取代的氨基酸和高对映选择性。该方法可以大规模制备此类氨基酸，以进行广泛的结构活性研究。
• MACROCYCLIC COMPOUNDS USEFUL AS BASE INHIBITORS
  申请人：Betschart Claudia

  公开号：US20090029960A1

  公开（公告）日：2009-01-29

  The invention relates to novel macrocyclic compounds of the formula in which all of the variables are as defined in the specification, in free base form or in acid addition salt form, to their preparation, to their use as medicaments and to medicaments comprising them.

  该发明涉及一种新型的大环化合物，其公式如下，在自由碱基形式或酸盐形式下，其中所有变量如规范中所定义，其制备方法，用作药物的方法以及包含它们的药物。
• Macrocyclic Compounds and Compositions Useful as Bace Inhibitors
  申请人：Lerchner Andreas

  公开号：US20080214526A1

  公开（公告）日：2008-09-04

  The invention relates to novel macrocyclic compounds of the formula in which R 1 , R 3 , V 1 , V 2 , X 1 , X 2 , Y, Z, Ar, AA and n are as defined in the specification, the number of ring atoms included in the macrocyclic ring being 14, 15, 16, 17 or 18, in free base form or in acid addition salt form, to their preparation, to their use as medicaments and to medicaments comprising them.

  本发明涉及新型大环化合物的公式，其中R1、R3、V1、V2、X1、X2、Y、Z、Ar、AA和n如规范中所定义，大环环中包含的环原子数为14、15、16、17或18，在自由碱形式或酸盐形式下，它们的制备，它们作为药物的用途以及包含它们的药物。
• WO2006/74940
  申请人：——

  公开号：——

  公开（公告）日：——