(S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester | 192211-88-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester
• 英文别名: [(2R,3S)-4-[(4S,5R,13S,15S)-4-hydroxy-13-methyl-5-(2-methylpropyl)-2,12,14-trioxo-15-propan-2-yl-1-oxa-6,11-diazacyclopentadec-6-yl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutan-2-yl] (2S)-2-[acetyl(methyl)amino]-3-(4-methoxyphenyl)propanoate
• CAS: 192211-88-4
• 化学式: C₄₂H₆₆N₄O₁₂
• 分子量: 819.006
• InChiKey: HLHUIFCCTXTKJY-QDWLPJPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  58.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  207.18
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 (S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-amino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Synthesis of a Reduced Ring Analog of Didemnin B

  摘要：

  As part of investigations directed toward the determination of the essential/nonessential structural features for the bioactivities of didemnin B, we designed a reduced ring analog in which three moieties, namely the tyrosine side chain, the isostatine hydroxyl, and the side chain (L-lactyl-L-prolyl-N-Me-D-leucine), were in their presumed bioactive conformation. In designing the reduced ring analog, we eliminated the leucine-proline portion of the macrocycle core and replaced if with an n-butyl linker in order to elucidate its role. According to MM2 calculations (MacroModel molecular modeling), this analog was of lower energy than the natural product didemnin B, and both structures were superimposable. The synthetic strategy involved four disconnections. Macrocyclization was accomplished at the activated carboxylic acid of the alpha-(alpha-hydroxyisovaleryl)-propionyl unit (HIP) and the protected amine of the n-butyl linker using a modification of Schmidt's protocol. After selective deprotection of the hydroxyl and amino groups of the macrocycle, the peptide side chain was introduced using (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) as the activating reagent.

  DOI：

  10.1021/jo9623696
• 作为产物：
  描述：

  Ac-N(Me)Tyr(Me)-(1).Boc-Thr(1)-OBn 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 9.5h， 生成 (S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester
  参考文献：
  名称：

  Synthesis of a Reduced Ring Analog of Didemnin B

  摘要：

  As part of investigations directed toward the determination of the essential/nonessential structural features for the bioactivities of didemnin B, we designed a reduced ring analog in which three moieties, namely the tyrosine side chain, the isostatine hydroxyl, and the side chain (L-lactyl-L-prolyl-N-Me-D-leucine), were in their presumed bioactive conformation. In designing the reduced ring analog, we eliminated the leucine-proline portion of the macrocycle core and replaced if with an n-butyl linker in order to elucidate its role. According to MM2 calculations (MacroModel molecular modeling), this analog was of lower energy than the natural product didemnin B, and both structures were superimposable. The synthetic strategy involved four disconnections. Macrocyclization was accomplished at the activated carboxylic acid of the alpha-(alpha-hydroxyisovaleryl)-propionyl unit (HIP) and the protected amine of the n-butyl linker using a modification of Schmidt's protocol. After selective deprotection of the hydroxyl and amino groups of the macrocycle, the peptide side chain was introduced using (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) as the activating reagent.

  DOI：

  10.1021/jo9623696