(S)-N-((S)-1-amino-3-hydroxy-1-oxopropan-2-yl)-2-((S)-3-methyl-4-((4-nitrophenyl)sulfonyl)-2-oxo-3,4-dihydropyrazin-1(2H)-yl)propanamide | 1417605-10-7

• 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: (S)-N-((S)-1-amino-3-hydroxy-1-oxopropan-2-yl)-2-((S)-3-methyl-4-((4-nitrophenyl)sulfonyl)-2-oxo-3,4-dihydropyrazin-1(2H)-yl)propanamide
• CAS: 1417605-10-7
• 化学式: C₁₇H₂₁N₅O₈S
• 分子量: 455.448
• InChiKey: FBBIIOPPKQWKJC-MJVIPROJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.36
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  193.25
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以20.1 mg的产率得到(S)-N-((S)-1-amino-3-hydroxy-1-oxopropan-2-yl)-2-((S)-3-methyl-4-((4-nitrophenyl)sulfonyl)-2-oxo-3,4-dihydropyrazin-1(2H)-yl)propanamide
  参考文献：
  名称：

  Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis

  摘要：

  A protected aldehyde was attached via a two-carbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective formation of cyclic N-acyliminiums between the aldehyde and the neighboring peptide amide nitrogen. In the absence of an internal nucleophile, the cyclic iminiums formed dihydropyrazinones, a six-membered peptide backbone constraint between two peptide amides. In the presence of an internal nucleophile, tetrahydropyrazinopyrimidinediones or tetrahydroimidazopyrazinediones were formed via tandem N-acyliminium ion cyclization-nucleophilic addition. The outcome of this nucleophilic addition was dependent on the substituent on the nitrogen nucleophile.

  DOI：

  10.1021/co300125m

文献信息

• Polymer-Supported Stereoselective Synthesis of Tetrahydro-2<i>H</i>-oxazolo[3,2-<i>a</i>]pyrazin-5(3<i>H</i>)-ones from <i>N</i>-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums
  作者：Agustina La Venia、Bohumil Dolenský、Viktor Krchňák

  DOI：10.1021/co3001567

  日期：2013.3.11

  Ser/Thr/Cys-containing dipeptides were synthesized and subjected to acid-mediated tandem N-acylium ion cyclization–nucleophilic addition to yield tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones. The reaction conditions and building-block combinations for stereoselective synthesis of the newly formed asymmetric carbon were developed. The synthesis was fully compatible with solid-phase peptide synthesis, and the products

  合成了聚合物支撑的N-（2-氧代乙基）衍生的Ser / Thr / Cys含二肽，并进行了酸介导的串联N-酰基离子环化-亲核加成反应，生成了四氢-2 H-恶唑啉[3， 2 - α ]吡嗪-5（3 H）-一。开发了新形成的不对称碳的立体选择性合成的反应条件和结构单元组合。该合成与固相肽合成完全相容，并且产物用作构象受限的拟肽。自行车的无痕合成也被报告为这项工作的一部分。