N-benzyloxycarbonyl-L-tryptophan ethyl ester | 41844-69-3

• 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: N-benzyloxycarbonyl-L-tryptophan ethyl ester
• 英文别名: L-Z-Trp-OEt；ethyl (2S)-3-(1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 41844-69-3
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 366.417
• InChiKey: HBEYOADCZVIALX-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-L-tryptophan ethyl ester 在 palladium on activated charcoal 甲酸铵 作用下， 以 异丙醇 为溶剂， 反应 0.08h， 以90%的产率得到D-色氨酸乙酯盐酸盐
  参考文献：
  名称：

  Rapid microwave-assisted deprotection of N-Cbz and N-Bn derivatives

  摘要：

  Catalytic-transfer hydrogenation in ifo-propanol under microwave irradiation has been performed to rapidly deprotect N-Cbz and N-Bn derivatives. The method is particularly suitable for the synthesis of short peptides and can also be carried out on supported molecules. The rapid cleavage of chiral molecules derived from (S)-1-phenylethylamine can be very useful for asymmetric synthesis of nitrogen containing compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00969-8
• 作为产物：
  描述：

  N-Benzyloxycarbonyl-tryptophanethylester 以92%的产率得到
  参考文献：
  名称：

  MORINIERE, J. L.;DANREE, B.;LEMOINE, J.;GUY, A., SYNTH. COMMUN., 18,(1988) N 4, 441-444

  摘要：

  DOI：

文献信息

• Novel esterifying agents, and their production and use
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US03976635A1

  公开（公告）日：1976-08-24

  A process for esterifying organic carboxylic acids which comprises reacting an organic carboxylic acid with a carbonic acid ester of the formula: ##EQU1## wherein R is an organic group and X and Y are each a negative group in the presence of a basic substance to make esterified the carboxyl group in the organic carboxylic acid. The process is advantageous in affording the objective carboxylic ester in a good yield within a short time by a simple operation under a mild reaction condition.

  一种酯化有机羧酸的方法，包括将有机羧酸与碳ic酸酯反应如下公式：其中R是有机基团，X和Y分别是负离子基团，在碱性物质存在下使有机羧酸中的羧基酯化。该工艺的优点在于，在温和的反应条件下，通过简单的操作，可以在短时间内以较高的收率获得所需的羧酸酯。
• Efficient esterification of carboxylic acids and phosphonic acids with trialkyl orthoacetate in ionic liquid
  作者：Tomonori Yoshino、Satomi Imori、Hideo Togo

  DOI：10.1016/j.tet.2005.09.147

  日期：2006.2

  environmentally friendly esterification of various carboxylic acids, phosphonic acids, and phosphinic acids with triethyl orthoacetate or trimethyl orthoacetate under neutral conditions in a typical room temperature ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate, was successfully carried out to provide the corresponding ethyl esters or methyl esters in high yields.

  在中性条件下，在典型的室温离子液体，即1-丁基-3-甲基咪唑六氟磷酸盐中，用原乙酸三乙酯或原乙酸三甲酯对各种羧酸，膦酸和次膦酸进行操作简单，廉价，有效和环保的酯化反应成功地进行了生产，以高收率提供了相应的乙酯或甲酯。
• Protonation-Assisted Conjugate Addition of Axially Chiral Enolates: Asymmetric Synthesis of Multisubstituted β-Lactams from α-Amino Acids
  作者：Tomoyuki Yoshimura、Masatoshi Takuwa、Keisuke Tomohara、Makoto Uyama、Kazuhiro Hayashi、Pan Yang、Ryuichi Hyakutake、Takahiro Sasamori、Norihiro Tokitoh、Takeo Kawabata

  DOI：10.1002/chem.201201339

  日期：2012.11.26

  prepared in a highly enantioselective manner through 4‐exo‐trig cyclization of axially chiral enolates generated from readily available α‐amino acids. Use of a weak base (metal carbonate) in a protic solvent (EtOH) is the key to the smooth production of β‐lactams. Use of the weak base is expected to generate the axially chiral enolates in a very low concentration, which undergo intramolecular conjugate addition

  具有4个和3个取代碳原子中心的β-内酰胺是通过4 - exo -trig环化由容易获得的α-氨基酸产生的轴向手性烯醇化物以高度对映选择性的方式制备的。在质子传递溶剂（EtOH）中使用弱碱（金属碳酸盐）是顺利生产β-内酰胺的关键。预期使用弱碱会产生非常低浓度的轴向手性烯醇盐，其经历分子内共轭物加成而不会发生分子间副反应。因此通过可逆的分子内共轭物加成反应形成了高张力的β-内酰胺烯醇（4 -exo-trig轴向手性烯醇盐的环化反应）在反应介质中迅速被EtOH质子化（而不是在后处理过程中），以生成高达97％ee的β-内酰胺。
• Environmentally Friendly Esterification of Carboxylic Acids with Triethyl Orthoacetate in Ionic Liquid
  作者：Hideo Togo、Tomonori Yoshino

  DOI：10.1055/s-2004-829058

  日期：——

  An operationally simple, inexpensive, efficient, and ­environmentally friendly esterification of carboxylic acids with triethyl orthoacetate under neutral conditions in a typical room ­temperature ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate, was carried out to provide the corresponding ethyl esters in high yields.

  在典型的室温离子液体1-丁基-3-甲基咪唑六氟磷酸盐中，通过三乙氧基乙酸与羧酸在中性条件下进行了一种操作简便、成本低廉、高效且环保的酯化反应，从而以高产率得到相应的乙酯。
• Moriniere, J. L.; Danree, B.; Lemoine, J., Synthetic Communications, 1988, vol. 18, # 4, p. 441 - 444
  作者：Moriniere, J. L.、Danree, B.、Lemoine, J.、Guy, A.

  DOI：——

  日期：——