(S)-N-benzyloxycarbonyl-β-(2-trimethylsilylethyl)-α-methyl-aspartate | 213473-96-2

• 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: (S)-N-benzyloxycarbonyl-β-(2-trimethylsilylethyl)-α-methyl-aspartate
• 英文别名: 1-O-methyl 4-O-(2-trimethylsilylethyl) (2S)-2-(phenylmethoxycarbonylamino)butanedioate
• CAS: 213473-96-2
• 化学式: C₁₈H₂₇NO₆Si
• 分子量: 381.501
• InChiKey: GYGQIKSNOBMGFN-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-N-benzyloxycarbonyl-β-(2-trimethylsilylethyl)-α-methyl-aspartate 在 palladium on activated charcoal 氢气 、 sodium carbonate 作用下， 以 氯仿 、 异丙醇 为溶剂， 反应 0.67h， 生成 (PheS,AspS)-N-9-fluorenylmethyloxycarbonyl-phenylalanyl-β-(2-trimethylsilylethyl)-α-methyl-aspartate
  参考文献：
  名称：

  Synthesis of a Model for Phycocyanin with Respect to the Acid-Base Chemistry between Protein and Chromophore

  摘要：

  Earlier investigations have shown that the cysteine adduct of phycocyanobilin dimethylester qualifies for intramolecular protonation [1]. In this context, the -Cys-Ala-Phe-Asp-tetrapeptide adduct of phycocyanobilin dimethylester was synthesized and examined for its protonation properties with respect to the zwitterionic interaction between chromophore and protein.

  DOI：

  10.1007/s007060070065
• 作为产物：
  描述：

  2-(三甲硅基)乙醇 、 N-Cbz-L-天冬氨酸 1-甲酯 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 2.0h， 以72%的产率得到(S)-N-benzyloxycarbonyl-β-(2-trimethylsilylethyl)-α-methyl-aspartate
  参考文献：
  名称：

  Synthesis of a Model for Phycocyanin with Respect to the Acid-Base Chemistry between Protein and Chromophore

  摘要：

  Earlier investigations have shown that the cysteine adduct of phycocyanobilin dimethylester qualifies for intramolecular protonation [1]. In this context, the -Cys-Ala-Phe-Asp-tetrapeptide adduct of phycocyanobilin dimethylester was synthesized and examined for its protonation properties with respect to the zwitterionic interaction between chromophore and protein.

  DOI：

  10.1007/s007060070065

文献信息

• Asymmetric Total Syntheses of Marine Cyclic Depsipeptide Halipeptins A–D
  作者：Shouyun Yu、Xianhua Pan、Dawei Ma

  DOI：10.1002/chem.200600383

  日期：2006.8.25

  Halipeptins A-D (1 a-d) are a family of natural cyclic depsipeptides isolated from marine sponges. Total syntheses of these four compounds are detailed in this report. The key elements in this synthesis include the elaboration of the polysubstituted decanoic acid parts by two asymmetric aldol reactions, assembly of the N-methyl-delta-hydroxyisoleucine residue by using either aza-Claisen rearrangement

  Halipeptins AD（1 ad）是从海洋海绵中分离出来的一类天然环状二肽。该报告详细介绍了这四种化合物的总合成。该合成中的关键元素包括通过两个不对称的羟醛缩合反应精制多取代的癸酸部分，使用aza-Claisen重排或天冬氨酸的甲基化作为关键步骤组装N-甲基-δ-羟基异亮氨酸残基以及进行大环化在多取代的癸酸丙氨酸位点。
• 1,2-Asymmetric induction in dianionic allylation reactions of amino acid derivatives-synthesis of functionally useful, enantiopure aspartates and constrained scaffolds
  作者：Stephen Hanessian、Roberto Margarita、Adrian Hall、Xuehong Luo

  DOI：10.1016/s0040-4039(98)00899-5

  日期：1998.8

  Dianions derived from N-Cbz aspartic acid esters undergo highly stereoselective anti allylation reactions at the unsubstituted carbon. The roles of additives, of the cation and of the electrophile were studied; Synthetic applications and potential utility in peptidomimetic design are also described. (C) 1998 Elsevier Science Ltd. All rights reserved.