(2S)-2-tert-Butoxycarbonylamino-4,4-dimethylhex-5-enoic acid methyl ester | 308807-00-3

• 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)-2-tert-Butoxycarbonylamino-4,4-dimethylhex-5-enoic acid methyl ester
• 英文别名: (S)-2-tert-Butoxycarbonylamino-4,4-dimethyl-hex-5-enoic acid methyl ester；2S-2-tert-butoxycarbonylamino-4,4-dimethyl-hex-5-enoic acid methyl ester；methyl (2S)-4,4-dimethyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-5-enoate
• CAS: 308807-00-3
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: OQDQZALXIPYJTD-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-tert-Butoxycarbonylamino-4,4-dimethylhex-5-enoic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以96%的产率得到(2S)-2-tert-Butoxycarbonylamino-4,4-dimethylhexanoic acid methyl ester
  参考文献：
  名称：

  A new route to hydrophobic amino acids using copper-promoted reactions of serine-derived organozinc reagents

  摘要：

  铜催化的丝氨酸衍生的锌试剂1与烯丙基亲电试剂反应，生成的产品源于形式上的SN2和SN2'途径。这些构造异构体可以直接分离，或者在(2S)-2-叔丁氧羰基氨基-6-甲基庚-5-烯酸甲酯（11）和(2S)-2-叔丁氧羰基氨基-4,4-二甲基己-5-烯酸甲酯（12）的情况下，通过选择性环氧化11来分离。双键的氢化，随后保护基团的调控，允许合成Fmoc保护的氨基酸3-7，准备用于自动化多肽合成。

  DOI：

  10.1039/b007032g
• 作为产物：
  描述：

  (2S)-2-tert-Butoxycarbonylamino-4,4-dimethylhexanoic acid methyl ester 生成 (2S)-2-tert-Butoxycarbonylamino-4,4-dimethylhex-5-enoic acid methyl ester
  参考文献：
  名称：

  Cysteine protease inhibitors

  摘要：

  公式（IV）的翻译如下： 其中： R1=R′C(O)，R′SO2， R′=含有0-4个来自S、O和N的杂原子的8-12元环系统，可以选择饱和或不饱和的双环，可选地取代最多四个从下面的a)、b)和c)组中独立选择的取代基；或 R′=含有0-3个来自S、O和N的杂原子的5-7元环，该单环至少带有从a)组和/或c)组中选择的一个取代基，并且可选地带有从b)组中选择的一个或两个进一步的取代基； R4=H，C1-7-烷基，Ar-C1-7-烷基，Ar，C3-7-环烷基；C2-7-烯基； R3=C1-7-烷基，C2-C7烯基，C2-C7烯基，C3-7-环烷基，Ar-C1-7-烷基，Ar； R5=C1-7-烷基，卤素，Ar-C1-7-烷基，C1-3-烷基-CONR3R4或体积庞大的胺 R6为H，C1-7-烷基，Ar-C1-7-烷基，C1-3-烷基-SO2-R ix ，C1-3-烷基-C(O)—NHR ix 或CH 2 XAr q为0或1 具有作为半胱氨酸蛋白酶抑制剂的实用性，例如卡特普辛K和疟原虫蛋白酶。

  公开号：

  US20030186962A1

文献信息

• Branched amino acids
  申请人：——

  公开号：US20030171434A1

  公开（公告）日：2003-09-11

  The invention relates to novel branched amino acids and novel methods for their production. The amino acids are useful in the preparation of non-natural peptides and peptidomimetics, by efficient synthesis methodology allowing good enantiomeric specificity at the alpha carbon. Typically the stereochemistry at the alpha carbon is at least 85%, preferably at least 95%, such as in excess of 99% enantiomerically pure. L-stereochemistry at this location is convenient as most biological interactions will favour this configuration, but the invention also extends to enantiomerically enriched and preferably at least 85%, preferably at least 95% such as at least 99% enantiomerically pure D stereoconfiguration. Compounds of the invention will find utility in the preparation of non-natural peptides and peptidomimetics, such as those used in the exploration of receptor specificity and activity or in peptidomimetic inhibitors of enzyme function. The compounds of the invention are built into such peptides/peptidomimetics using standard peptide chemistry.

  该发明涉及新型分支型氨基酸及其制备的新方法。这些氨基酸在非天然肽和肽类似物的制备中非常有用，通过高效的合成方法，在α碳处具有良好的对映体特异性。通常，α碳的立体化学至少为85％，最好至少为95％，例如超过99％的对映纯。在这个位置的L-立体化学很方便，因为大多数生物相互作用都会偏向于这种配置，但该发明也扩展到对映富集的、优选至少为85％、最好至少为95％，例如至少为99％的对映纯D立体构型。该发明的化合物将在标准肽化学中被构建成这样的肽/肽类似物。该发明的化合物将在非天然肽和肽类似物的制备中发挥作用，例如在探索受体特异性和活性或肽类似物酶功能抑制剂中使用。
• Furanone derivatives as inhibitors of Cathepsin S
  申请人：Medivir UK Ltd

  公开号：EP1413580A1

  公开（公告）日：2004-04-28

  Cathepsin S is a highly active cysteine protease belonging to the papain superfamily. It is found mainly in lymph nodes, spleen, and macrophages and this limited occurrence suggests the potential involvement of this enzyme in the pathogenesis of degenerative disease. The invention relates to novel protease inhibitors, particularly inhibitors of the cysteine proteases of the papain superfamily and more particularly to Cathepsin S. The inhibitors are Furanone derivatives of Formula (II) which have a characteristic non-hydrogen substituent R5. They are selective over other members of the family and in particular show selectivity over other members of the Cathepsin family such as L and K.

  Cathepsin S 是一种属于木瓜蛋白酶超家族的高活性半胱氨酸蛋白酶。它主要存在于淋巴结、脾脏和巨噬细胞中，这种有限的存在表明这种酶可能参与了变性疾病的发病机制。本发明涉及新型蛋白酶抑制剂，特别是木瓜蛋白酶超家族半胱氨酸蛋白酶的抑制剂，尤其是 Cathepsin S。它们对该家族的其他成员具有选择性，特别是对酪蛋白酶家族的其他成员如 L 和 K 具有选择性。
• FURANONE DERIVATIVES AS INHIBITORS OF CATHEPSIN S
  申请人：Medivir UK Ltd

  公开号：EP1178986A2

  公开（公告）日：2002-02-13
• CYSTEINE PROTEASE INHIBITORS
  申请人：Medivir UK Ltd

  公开号：EP1345931A2

  公开（公告）日：2003-09-24
• [EN] FURANONE DERIVATIVES AS INHIBITORS OF CATHEPSIN S<br/>[FR] DERIVES FURANONES INHIBITEURS DE CATHEPSINE S
  申请人：MEDIVIR UK LTD

  公开号：WO2000069855A2

  公开（公告）日：2000-11-23

  Cathepsin S is a highly active cysteine protease belonging to the papain superfamily. It is found mainly in lymph nodes, spleen, and macrophages and this limited occurrence suggests the potential involvement of this enzyme in the pathogenesis of degenerative disease. The invention relates to novel protease inhibitors, particularly inhibitors of the cysteine proteases of the papain superfamily and more particularly to Cathepsin S. The inhibitors are Furanone derivatives of Formula (II) which have a characteristic non-hydrogen substituent R5. They are selective over other members of the family and in particular show selectivity over other members of the Cathepsin family such as L and K.