[(3S,4S,5S)-4-(methoxymethoxy)-2,5-dimethyl-6-oxo-6-(2,3,4,5,6-pentafluorophenoxy)hexan-3-yl] (3S,4R)-6-methyl-4-[(2-methylpropan-2-yl)oxycarbonyl-[4-(phenylmethoxycarbonylamino)butyl]amino]-3-tri(propan-2-yl)silyloxyheptanoate | 192211-89-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: [(3S,4S,5S)-4-(methoxymethoxy)-2,5-dimethyl-6-oxo-6-(2,3,4,5,6-pentafluorophenoxy)hexan-3-yl] (3S,4R)-6-methyl-4-[(2-methylpropan-2-yl)oxycarbonyl-[4-(phenylmethoxycarbonylamino)butyl]amino]-3-tri(propan-2-yl)silyloxyheptanoate
• CAS: 192211-89-5
• 化学式: C₅₀H₇₇F₅N₂O₁₁Si
• 分子量: 1005.25
• InChiKey: HEAGSXQBXDWGEF-FOLLZQILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.79
• 重原子数：
  69
• 可旋转键数：
  32
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(3S,4S,5S)-4-(methoxymethoxy)-2,5-dimethyl-6-oxo-6-(2,3,4,5,6-pentafluorophenoxy)hexan-3-yl] (3S,4R)-6-methyl-4-[(2-methylpropan-2-yl)oxycarbonyl-[4-(phenylmethoxycarbonylamino)butyl]amino]-3-tri(propan-2-yl)silyloxyheptanoate 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 二甲基溴化硼 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 戴斯-马丁氧化剂 、 4-吡咯烷基吡啶 、 环己烯 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 64.0h， 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
• 作为产物：
  描述：

  苯甲氧羰酰琥珀酰亚胺 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 potassium permanganate 、 sodium dihydrogenphosphate 、 钾硼氢 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 80.5h， 生成 [(3S,4S,5S)-4-(methoxymethoxy)-2,5-dimethyl-6-oxo-6-(2,3,4,5,6-pentafluorophenoxy)hexan-3-yl] (3S,4R)-6-methyl-4-[(2-methylpropan-2-yl)oxycarbonyl-[4-(phenylmethoxycarbonylamino)butyl]amino]-3-tri(propan-2-yl)silyloxyheptanoate
  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

文献信息

• Synthesis of a Reduced Ring Analog of Didemnin B
  作者：Joshi M. Ramanjulu、Xiaobin Ding、Madeleine M. Joullié、Wen-Ren Li

  DOI：10.1021/jo9623696

  日期：1997.7.1

  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.