(2S,3S)-2-{[(S)-1-((S)-2-Amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester | 1027292-44-9

• 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: (2S,3S)-2-{[(S)-1-((S)-2-Amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester
• 英文别名: H-Phe-Pro-aThr-OMe；methyl (2S,3S)-2-[[(2S)-1-[(2S)-2-amino-3-phenylpropanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoate
• CAS: 1027292-44-9
• 化学式: C₁₉H₂₇N₃O₅
• 分子量: 377.44
• InChiKey: XEROONKLBBZVHT-TUUVXOQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-{[(S)-1-((S)-2-Amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester 在 palladium dihydroxide sodium hydroxide 、 伯吉斯试剂 、 偶氮二甲酸二异丙酯 、 五氟苯基二苯基磷酸酯 、 四丁基氟化铵 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 cyclo[D-Val-Ser(oxaz)-D-Phe-Ser(oxaz)-Phe-Pro-Allo-Thr(oxaz)]
  参考文献：
  名称：

  Total Synthesis and Assignment of Configuration of Lissoclinamide 7

  摘要：

  The first total synthesis of lissoclinamide 7, a 21-membered cyclopeptide isolated from Lissoclinum bistratum, was accomplished in 23 steps and 4.4% overall yield. The extraordinary configurational lability of the thiazoline segments was overcome by a novel strategy combining the use of the Burgess reagent for multiple simultaneous oxazoline and thiazoline formations and an efficient oxazoline --> thiazoline heterocycle interconversion. In addition to the total synthesis, this work highlights the scope of alternative strategies toward Lissoclinum peptides and presents the preparation of analogues for SAR studies of the cytotoxic effects of this family of marine natural products.

  DOI：

  10.1021/ja962859f
• 作为产物：
  描述：

  Z-Phe-O-COO-isoBu 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 lithium hydroxide 、 伯吉斯试剂 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 8.42h， 生成 (2S,3S)-2-{[(S)-1-((S)-2-Amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester
  参考文献：
  名称：

  Total Synthesis and Assignment of Configuration of Lissoclinamide 7

  摘要：

  The first total synthesis of lissoclinamide 7, a 21-membered cyclopeptide isolated from Lissoclinum bistratum, was accomplished in 23 steps and 4.4% overall yield. The extraordinary configurational lability of the thiazoline segments was overcome by a novel strategy combining the use of the Burgess reagent for multiple simultaneous oxazoline and thiazoline formations and an efficient oxazoline --> thiazoline heterocycle interconversion. In addition to the total synthesis, this work highlights the scope of alternative strategies toward Lissoclinum peptides and presents the preparation of analogues for SAR studies of the cytotoxic effects of this family of marine natural products.

  DOI：

  10.1021/ja962859f

文献信息

• Total Synthesis and Assignment of Configuration of Lissoclinamide 7
  作者：Peter Wipf、Paul C. Fritch

  DOI：10.1021/ja962859f

  日期：1996.1.1

  The first total synthesis of lissoclinamide 7, a 21-membered cyclopeptide isolated from Lissoclinum bistratum, was accomplished in 23 steps and 4.4% overall yield. The extraordinary configurational lability of the thiazoline segments was overcome by a novel strategy combining the use of the Burgess reagent for multiple simultaneous oxazoline and thiazoline formations and an efficient oxazoline --> thiazoline heterocycle interconversion. In addition to the total synthesis, this work highlights the scope of alternative strategies toward Lissoclinum peptides and presents the preparation of analogues for SAR studies of the cytotoxic effects of this family of marine natural products.