benzyl N-[(5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-[21-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoyl]-8,23-dioxo-2-oxa-7,10,14,17,21,24-hexazatetracyclo[23.2.2.23,6.214,17]tritriaconta-1(27),3(33),4,6(32),25,28-hexaen-10-yl]-6-oxohexyl]carbamate | 1133693-82-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: benzyl N-[(5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-[21-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoyl]-8,23-dioxo-2-oxa-7,10,14,17,21,24-hexazatetracyclo[23.2.2.23,6.214,17]tritriaconta-1(27),3(33),4,6(32),25,28-hexaen-10-yl]-6-oxohexyl]carbamate
• CAS: 1133693-82-9
• 化学式: C₆₄H₈₈N₁₀O₁₃
• 分子量: 1205.46
• InChiKey: JTOXHVGDPIWTGL-PJYGOTMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  87
• 可旋转键数：
  24
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  268
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  benzyl N-[(5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-[21-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoyl]-8,23-dioxo-2-oxa-7,10,14,17,21,24-hexazatetracyclo[23.2.2.23,6.214,17]tritriaconta-1(27),3(33),4,6(32),25,28-hexaen-10-yl]-6-oxohexyl]carbamate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Architectural Chemistry: Synthesis of Topologically Diverse Macromulticycles by Sequential Multiple Multicomponent Macrocyclizations

  摘要：

  How can conformationally restricted polyvalent molecules be accessed rapidly? A sequential approach involving two multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs) with up to five Ugi-four-component reactions (Ugi-4CR) has been developed to produce nonsymmetric macromulticycles. Topologically diverse structures, such as nonsymmetric cryptands and clam-,and igloo-shaped macromulticycles were obtained in reaction sequences that comprise the incorporation of up to 13 building blocks by forming 20 new bonds without purification of intermediates. Cryptands were produced by a sequential-MiB procedure in which the Ugi-type functional groups of the second MiB are attached to the peptoid backbones from the first multicomponent macrocyclization. These macrobicycles show two completely new features; i.e., three different tether chains can be obtained in one pot, and tertiary amide bonds are used as bridgeheads. Alternatively, the same reaction sequence, i.e., MiB/deprotection/MiB, can be used to produce clam-shaped macrobicycles, demonstrated with a tetrafunctional cholanic steroid as a hinge moiety. Macrotetracycles endowed with igloo-type topologies are accessible by an advanced protocol featuring consecutive double and 3-fold Ugi-4CR-based macrocyclizations. Other building blocks than cholanic steroids employed include aryl, heterocyclic, polyether, and other recognition motifs. The examples given are a first-generation demonstration of an "architectural chemistry" that allows to construct three-dimensional multimotif covalent molecular "buildings" of unprecedented complexity by design.

  DOI：

  10.1021/ja809005k
• 作为产物：
  描述：

  4,4'-diisocyanodiphenyl ether 、 1,4-双(3-氨基丙基)哌嗪 、 聚合甲醛 、 N-Boc-N'-Cbz-L-赖氨酸 以 甲醇 为溶剂， 反应 1.5h， 生成 benzyl N-[(5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-[21-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoyl]-8,23-dioxo-2-oxa-7,10,14,17,21,24-hexazatetracyclo[23.2.2.23,6.214,17]tritriaconta-1(27),3(33),4,6(32),25,28-hexaen-10-yl]-6-oxohexyl]carbamate
  参考文献：
  名称：

  Architectural Chemistry: Synthesis of Topologically Diverse Macromulticycles by Sequential Multiple Multicomponent Macrocyclizations

  摘要：

  How can conformationally restricted polyvalent molecules be accessed rapidly? A sequential approach involving two multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs) with up to five Ugi-four-component reactions (Ugi-4CR) has been developed to produce nonsymmetric macromulticycles. Topologically diverse structures, such as nonsymmetric cryptands and clam-,and igloo-shaped macromulticycles were obtained in reaction sequences that comprise the incorporation of up to 13 building blocks by forming 20 new bonds without purification of intermediates. Cryptands were produced by a sequential-MiB procedure in which the Ugi-type functional groups of the second MiB are attached to the peptoid backbones from the first multicomponent macrocyclization. These macrobicycles show two completely new features; i.e., three different tether chains can be obtained in one pot, and tertiary amide bonds are used as bridgeheads. Alternatively, the same reaction sequence, i.e., MiB/deprotection/MiB, can be used to produce clam-shaped macrobicycles, demonstrated with a tetrafunctional cholanic steroid as a hinge moiety. Macrotetracycles endowed with igloo-type topologies are accessible by an advanced protocol featuring consecutive double and 3-fold Ugi-4CR-based macrocyclizations. Other building blocks than cholanic steroids employed include aryl, heterocyclic, polyether, and other recognition motifs. The examples given are a first-generation demonstration of an "architectural chemistry" that allows to construct three-dimensional multimotif covalent molecular "buildings" of unprecedented complexity by design.

  DOI：

  10.1021/ja809005k