N-triphenylmethyl-(L)-threonine | 80514-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-triphenylmethyl-(L)-threonine
• 英文别名: (2S,3R)-3-hydroxy-2-(tritylazaniumyl)butanoate
• CAS: 80514-76-7
• 化学式: C₂₃H₂₃NO₃
• 分子量: 361.441
• InChiKey: CBIIBFYYCAFENA-UTKZUKDTSA-N

物化性质

• 沸点：
  552.0±50.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-triphenylmethyl-(L)-threonine 在 Pd-BaSO₄ 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 氯仿 为溶剂， 生成 (2S,3S)-3-Methyl-1-trityl-aziridine-2-carboxylic acid [((S)-1-benzylcarbamoyl-2-phenyl-ethylcarbamoyl)-methyl]-amide
  参考文献：
  名称：

  Conjugation of Selenols with Aziridine-2-Carboxylic Acid-Containing Peptides

  摘要：

  描述了在含有氮丙啶-2-羧酸的多肽中添加苯硒醇的过程，从而扩大了对于这类电亲核性多肽底物开环的亲核体范围。该过程提供了一种生成有用的苯硒半胱氨酸衍生物和含α-硒-β-氨基酸的多肽的新策略。

  DOI：

  10.1055/s-2005-871972
• 作为产物：
  描述：

  L-苏氨酸 、 三苯基氯甲烷 在 三甲基氯硅烷 、 三乙胺 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 21.25h， 以59%的产率得到N-triphenylmethyl-(L)-threonine
  参考文献：
  名称：

  Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates

  摘要：

  Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para-methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding beta-methyl azalanthionines have, so far, been unsuccessful. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.011

文献信息

• Inhibitors of Hepatitis C Virus
  申请人：D'Andrea Stanley

  公开号：US20080107625A1

  公开（公告）日：2008-05-08

  Macrocyclic peptides are disclosed having the general formula: wherein R 3 , R 3 ′, R 4 , R 6 , R′, X, Q and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

  揭示了具有一般公式的大环肽： 其中描述了R3、R3'、R4、R6、R'、X、Q和W。还公开了包含这些化合物的组合物以及使用这些化合物抑制HCV的方法。
• Hepatitis C virus inhibitors
  申请人：D'Andrea Stanley

  公开号：US20070099825A1

  公开（公告）日：2007-05-03

  Macrocyclic peptides are disclosed having the general formula: wherein R′, R 3 , R 3′ , R 4 , R 6 , X, Q, and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

  大环肽被公开，具有一般的公式： 其中R'，R3，R3'，R4，R6，X，Q和W被描述。还公开了包含该化合物的组合物以及使用该化合物抑制HCV的方法。
• [EN] THIOPHENE-SUBSTITUTED TETRACYCLIC COMPOUNDS AND METHODS OF USE THEREOF FOR TREATMENT OF VIRAL DISEASES<br/>[FR] COMPOSÉS TÉTRACYCLIQUES À SUBSTITUTION THIOPHÈNE ET LEURS MÉHODES D'UTILISATION POUR LE TRAITEMENT DE MALADIES VIRALES
  申请人：MERCK SHARP & DOHME

  公开号：WO2014110706A1

  公开（公告）日：2014-07-24

  Thiophene-substituted tetracyclic compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein A, A', R2, R3, R4 and R5 are as defined herein. The compositions comprising at least one thiophene-substituted tetracyclic compound, and methods of using the thiophene-substituted tetracyclic compounds for treating or preventing HCV infection in a patient are also provided.

  式(I)的噻吩取代四环化合物及其药用可接受的盐，其中A、A'、R2、R3、R4和R5如本文所定义。还提供了包含至少一种噻吩取代四环化合物的组合物，以及使用这些噻吩取代四环化合物治疗或预防患者HCV感染的方法。
• Reaction of N-trityl amino acids with BOP: Efficient synthesis of t-butyl esters as well as N-trityl serine- and threonine-β-lactones
  作者：Karen M Sliedregt、Arie Schouten、Jan Kroon、Rob M.J Liskamp

  DOI：10.1016/0040-4039(96)00805-2

  日期：1996.6

  Upon exposure to methoxymethylamine and BOP, the stable hydroxybenzotriazolyl amide of TrPheOH was isolated instead of the expected Weinreb amide. This amide behaves as an active amide similar to the Weinreb amide and could be used, among others, for the synthesis of t-Bu esters. Reaction of N-trityl serine and threonine led to the corresponding β-lactones in unprecedented high yields.

  暴露于甲氧基甲基胺和BOP后，分离出稳定的TrPheOH羟基苯并三唑基酰胺，而不是预期的Weinreb酰胺。该酰胺表现出类似于Weinreb酰胺的活性酰胺，并且可以用于合成叔丁基酯。N-三苯甲基丝氨酸和苏氨酸的反应以前所未有的高收率产生了相应的β-内酯。
• Amino acid derivatives and processes for preparation thereof
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0193904A2

  公开（公告）日：1986-09-10

  Acompound of the formula: wherein R1 is hydrogen, amino or a protected amino group, R2 is hydrogen, carboxy or a protected carboxy group, R3 is hydrogen, carboxy or a protected carboxy group, R4 is lower alkyl, amino(lower)alkyl, protected amino-(lower)alkyl, carbamoyl(lower)alkyl or protected carbamoyl(lower)alkyl, R5 is hydrogen or lower alkyl, and R6 is hydrogen, ar(lower)alkyl which may have suitable substituent(s) or heterocyclic(lower)alkyl, and pharmaceutically acceptable salts thereof, processes for its preparation and pharmaceutical compositions comprising it as an effective ingredient. The invention also comprises compounds of the formula useful for preparing the above compounds and a biologically pure culture of the microorganism Discosia sp. F-11 809.

  式中的化合物： 式中 R1 是氢、氨基或受保护的氨基、 R2 是氢、羧基或受保护的羧基 R3 是氢、羧基或受保护的羧基 R4 是低级烷基、氨基（低级）烷基、受保护氨基（低级）烷基、氨基甲酰基（低 级）烷基或受保护氨基甲酰基（低级）烷基、 R5 是氢或低级烷基，以及 R6 是氢、可具有适当取代基的芳基（低级）烷基或杂环（低级）烷基，及其药学上可接受的盐、其制备工艺和包含其作为有效成分的药物组合物。本发明还包括用于制备上述化合物的式 用于制备上述化合物和微生物 Discosia sp.F-11 809 的生物纯培养物。