Cbz-β-cyanoalanyl benzyl ester | 82215-18-7

• 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: Cbz-β-cyanoalanyl benzyl ester
• 英文别名: (S)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-cyanopropanoate；benzyl (2S)-3-cyano-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 82215-18-7
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: RGPNTUFXRPJOBA-KRWDZBQOSA-N

物化性质

• 沸点：
  561.1±50.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  88.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-苄氧羰基-L-天冬酰胺 在 碳酸氢钠 、 对甲苯磺酰氯 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 生成 Cbz-β-cyanoalanyl benzyl ester
  参考文献：
  名称：

  氨基酸替代：间接合成含有硫天冬酰胺残基的肽的方法

  摘要：

  受保护的五肽Boc-Tan-Cys（PMB）-Pro-Leu-GlynH 2 1和相关的硫天冬酰胺基化合物是通过相应的β-氰基丙氨酰基前体经H 2 S / NH 3处理而间接制备的。硫天冬酰胺（Tan）衍生物的光学纯度通过两种不同的方法进行了评估。

  DOI：

  10.1016/s0040-4039(00)86771-4

文献信息

• An Improved Synthesis of β-Cyano-l-Alanine Esters and Amides
  作者：Guoxin Wang、Zigang Li、Longjian Chen、Xiaodan Cai、Ming Luo

  DOI：10.1055/s-0035-1560489

  日期：——

  We have developed a novel, mild, efficient, and scalable protocol for the synthesis of N-protected -cyano-l-alanine esters or amides from N-protected l-asparagin. This protocol avoided the use of toxic or unpleasant reagents and was easy to operate in laboratory.
• A Concise Synthesis of β-Asparaginyladenylate
  作者：Yun Ding、Jianqiang Wang、Sheldon M. Schuster、Nigel G. J. Richards

  DOI：10.1021/jo025510l

  日期：2002.6.1

  Stable analogues of acyladenylate intermediates, such as N-acylphosphoramidates, are useful probes of tRNA aminoacylation and enzyme mechanism, and have potential application as enzyme inhibitors. We now report a concise, "one-pot" synthesis of beta-asparaginyladenylate using a novel coupling protocol that yields the target N-acylphosphoramidate in three reactions from readily available precursors. This simple synthetic procedure may represent a general approach for the preparation of functionalized N-acylphosphoramidates from amides that do not undergo coupling under the conditions of existing literature protocols.
• Amino acids surrogates: an indirect method for the synthesis of peptides containing the thioasparaginyl residue
  作者：Hossain Saneii、Arno F. Spatola

  DOI：10.1016/s0040-4039(00)86771-4

  日期：1982.1

  The protected pentapeptide, Boc-Tan-Cys(PMB)-Pro-Leu-GlynH21 and related thioasparaginyl compounds were prepared by an indirect method from their corresponding β-cyanoalanyl precursors by treatment with H2S/NH3. The optical purities of thioasparagine (Tan) derivatives were evaluated by two different approaches.

  受保护的五肽Boc-Tan-Cys（PMB）-Pro-Leu-GlynH 2 1和相关的硫天冬酰胺基化合物是通过相应的β-氰基丙氨酰基前体经H 2 S / NH 3处理而间接制备的。硫天冬酰胺（Tan）衍生物的光学纯度通过两种不同的方法进行了评估。