N-tert-butoxycarbonyl-S-benzylcysteinamide | 98929-91-0

• 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: N-tert-butoxycarbonyl-S-benzylcysteinamide
• 英文别名: Boc-Cys(Bzl)-NH2；tert-butyl N-[(2R)-1-amino-3-benzylsulfanyl-1-oxopropan-2-yl]carbamate
• CAS: 98929-91-0
• 化学式: C₁₅H₂₂N₂O₃S
• 分子量: 310.417
• InChiKey: WEWYMQAVUSASQT-LBPRGKRZSA-N

物化性质

• 沸点：
  501.6±50.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-S-benzylcysteinamide 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 ethyl N-tert-butoxycarbonyl-S-benzylcysteine-4-thiazolecarboxylate
  参考文献：
  名称：

  总合成诺西肽。噻唑片段的合成

  摘要：

  描述了从天然产物中制备三种新的噻唑衍生物的方法，以及2-氨基甲基-4-噻唑羧酸乙酯的合成方面的改进。

  DOI：

  10.1002/jhet.5570320436
• 作为产物：
  描述：

  Boc-S-苄基-L-半光氨酸 在 3-hydroxy-1,2,3-benzotriazin-4(3H)-one ammonium salt 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到N-tert-butoxycarbonyl-S-benzylcysteinamide
  参考文献：
  名称：

  Efficient, Racemization-Free Amidation of Protected Amino Acids

  摘要：

  将 L-亮氨酸、S-苄基-L-半胱氨酸和 Nt-(2,4-二硝基苯基)-L-组氨酸的 N-叔丁氧羰基衍生物与 3-羟基-1,2,3-苯并三嗪-4(3H)-酮和 N-羟基琥珀酰亚胺的结晶铵盐、甲铵盐和乙铵盐进行酰胺化反应，得到相应的氨基酸酰胺，产率高，光学纯度好。

  DOI：

  10.1055/s-1992-26093

文献信息

• The preparation of optically active α-amino 4H-[1,2,4]oxadiazol-5-ones from optically active α-amino acids
  作者：John E. Mangette、Matthew R. Johnson、Van-Duc Le、Rajesh A. Shenoy、Howard Roark、Michael Stier、Thomas Belliotti、Thomas Capiris、Peter R. Guzzo

  DOI：10.1016/j.tet.2009.09.045

  日期：2009.11

  Optically active α-amino 4H-[1,2,4]oxadiazol-5-ones (oxadiazolones) were prepared from optically active α-amino acids in five synthetic steps. The oxadiazolone moiety serves as a bioisosteric replacement for the carboxylic acid. Incorporation of an α-amino oxadiazolone into a representative dipeptide mimic is described.

  在五个合成步骤中，由旋光性α-氨基酸制备旋光性α-氨基4 H- [1,2,4]恶二唑-5-酮（恶二唑酮）。恶二唑酮部分用作羧酸的生物立体替代物。描述了将α-氨基恶二唑酮掺入代表性的二肽模拟物中。
• Efficient, Racemization-Free Amidation of Protected Amino Acids
  作者：Csaba Somlai、Gyula Szókán、Lajos Baláspiri

  DOI：10.1055/s-1992-26093

  日期：——

  N-tert-Butoxycarbonyl derivatives of L-leucine, S-benzyl-L-cysteine and Nt-(2,4-dinitrophenyl)-L-histidine were amidated with crystalline ammonium, methylammonium, and ethylammonium salts of 3-hydroxy-1,2,3-benzotriazin-4(3H)-one and N-hydroxysuccinimide to give the corresponding amino acid amides in good yield and with good optical purity.

  将 L-亮氨酸、S-苄基-L-半胱氨酸和 Nt-(2,4-二硝基苯基)-L-组氨酸的 N-叔丁氧羰基衍生物与 3-羟基-1,2,3-苯并三嗪-4(3H)-酮和 N-羟基琥珀酰亚胺的结晶铵盐、甲铵盐和乙铵盐进行酰胺化反应，得到相应的氨基酸酰胺，产率高，光学纯度好。
• Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics
  作者：Gundala Chennakrishnareddy、Govindappa Nagendra、Hosahalli P. Hemantha、Ushati Das、Tayur N. Guru Row、Vommina V. Sureshbabu

  DOI：10.1016/j.tet.2010.06.082

  日期：2010.8

  Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The H-1 NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenour-eido derivatives is free from racemization. (C) 2010 Elsevier Ltd. All rights reserved.
• <i>N</i>-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides
  作者：Vommina V. Sureshbabu、Shankar A. Naik、H. P. Hemantha、N. Narendra、Ushati Das、Tayur N. Guru Row

  DOI：10.1021/jo900675s

  日期：2009.8.7

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).
• Total synthesis of nosiheptide. Synthesis of thiazole fragments
  作者：Karen Koerber-Plé、Georges Massiot

  DOI：10.1002/jhet.5570320436

  日期：1995.7

  The preparation of three new thiazole derivatives from natural products is described, as well as improvements in the synthesis of ethyl 2-aminomethyl-4-thiazolecarboxylate.

  描述了从天然产物中制备三种新的噻唑衍生物的方法，以及2-氨基甲基-4-噻唑羧酸乙酯的合成方面的改进。