methyl (2S)-1-[(2S)-1-(tert-butylamino)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxylate | 1446348-63-5

• 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: methyl (2S)-1-[(2S)-1-(tert-butylamino)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxylate
• CAS: 1446348-63-5
• 化学式: C₁₃H₂₂N₂O₄
• 分子量: 270.329
• InChiKey: RFBRATANAACYJP-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  dimethyl ((S)-1-(tert-butylamino)-1-oxopropan-2-yl)-L-glutamate 以 甲苯 为溶剂， 以71%的产率得到methyl (2S)-1-[(2S)-1-(tert-butylamino)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  A Biomimetic Approach to the Synthesis of Terpene-Amino Acid Conjugates. The Ugi Reaction in the Hypothetical Biosynthesis of Marine Natural Products

  摘要：

  A unique pathway for the biosynthesis of the marine sponge terpenes, exigurin and boneratamides A-C, is proposed. Based on this proposal, a biomimetic strategy on key Ugi coupling reactions between terpene isocyanides and amino acids was developed for construction of the core structures of exigurin and boneratamides A-C.

  DOI：

  10.3987/com-16-13442

文献信息

• A Biomimetic Approach to Terpenes Isolated from Marine Sponges: a Ugi Coupling Reaction in a Hypothetical Biosynthesis
  作者：Yoshiyasu Ichikawa、Kenta Saito、Ayumu Nishimori、Hiyoshizo Kotsuki、Keiji Nakano

  DOI：10.1055/s-0032-1318305

  日期：——

  A unique pathway for the biosynthesis of marine sponge terpenes is proposed. Based on this proposal, a biomimetic approach using a Ugi coupling reaction has been designed and applied to the efficient construction of the right-side, peptide-like portions of boneratamides and exigurin.