(S)-2-Benzyloxycarbonylamino-3-methyl-2-(2-oxo-ethyl)-butyric acid methyl ester | 847154-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-Benzyloxycarbonylamino-3-methyl-2-(2-oxo-ethyl)-butyric acid methyl ester
• CAS: 847154-28-3
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: IBYHWPSPKUDJMN-INIZCTEOSA-N

物化性质

• 沸点：
  460.4±45.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzyloxycarbonylamino-3-methyl-2-(2-oxo-ethyl)-butyric acid methyl ester 在 palladium on activated charcoal 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 、 环己烯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 甲苯 、 苯 为溶剂， 反应 11.25h， 生成 (S)-6-Azido-2-[2-((S)-4-benzyl-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrrol-2-yl)-eth-(E)-ylideneamino]-2-(2,2-dimethoxy-ethyl)-hexanoic acid methyl ester
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974
• 作为产物：
  描述：

  (2S,4S)-2-tert-Butyl-4-isopropyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester 在 氢氧化钾 、 四(三苯基膦)钯 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 5,5-二甲基-1,3-环己二酮 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 37.0h， 生成 (S)-2-Benzyloxycarbonylamino-3-methyl-2-(2-oxo-ethyl)-butyric acid methyl ester
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974

文献信息

• Design, Synthesis, and Structural Analysis of <scp>d</scp>,<scp>l</scp>-Mixed Polypyrrolinones. 2. Macrocyclic Hexapyrrolinones
  作者：Amos B. Smith, III、Hui Xiong、Adam K. Charnley、Meinrad Brenner、Eugen F. Mesaros、Craig S. Kenesky、Luigi Di Costanzo、David W. Christianson、Ralph Hirschmann

  DOI：10.1021/ol101008y

  日期：2010.7.2

  The design, synthesis, and structural analysis of two macrocyclic D,L-alternating hexapyrrolinones have been achieved. These cyclic peptide mimics adopt a flat, hexagonal conformation, stabilized by intramolecular hydrogen bonding between adjacent pyrrolinone rings. Extensive NMR studies and X-ray analysis reveal, respectively, that the macrocyclic hexapyrrolinones aggregate in solution and in the solid state form staggered stacked nanotube-like assemblies.