benzyl (3-(4-(2-amino-2-oxoethyl)-3-oxo-3,4-dihydropyrazin-1(2H)-yl)-3-oxopropyl)carbamate | 1417604-40-0

• 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: benzyl (3-(4-(2-amino-2-oxoethyl)-3-oxo-3,4-dihydropyrazin-1(2H)-yl)-3-oxopropyl)carbamate
• CAS: 1417604-40-0
• 化学式: C₁₇H₂₀N₄O₅
• 分子量: 360.37
• InChiKey: MPNYOVPLMKSMEV-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  2-[(6S,9aS)-6-methyl-1-(4-methylphenyl)sulfonyl-4,7-dioxo-3,6,9,9a-tetrahydro-2H-pyrazino[1,2-a]pyrimidin-8-yl]acetamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以3.1 mg的产率得到benzyl 8-(2-amino-2-oxoethyl)-4,7-dioxooctahydro-1H-pyrazino[1,2-a]pyrimidine-1-carboxylate
  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