[(2S)-3-[1-[3-[(2S)-3-methoxy-3-oxo-2-(phenylmethoxycarbonylamino)propyl]-1-[(4-methoxyphenyl)methyl]indol-2-yl]imidazol-4-yl]-2-[[2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-[[(E)-N'-nitrocarbamimidoyl]amino]pentanoyl]amino]acetyl]amino]propyl] 2,2-dimethylpropanoate | 602308-92-9

• 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)-3-[1-[3-[(2S)-3-methoxy-3-oxo-2-(phenylmethoxycarbonylamino)propyl]-1-[(4-methoxyphenyl)methyl]indol-2-yl]imidazol-4-yl]-2-[[2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-[[(E)-N'-nitrocarbamimidoyl]amino]pentanoyl]amino]acetyl]amino]propyl] 2,2-dimethylpropanoate
• CAS: 602308-92-9
• 化学式: C₅₂H₆₇N₁₁O₁₃
• 分子量: 1054.17
• InChiKey: VLQCZSSBNIPDKP-FTMPZMEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  76
• 可旋转键数：
  30
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  316
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(2S)-3-[1-[3-[(2S)-3-methoxy-3-oxo-2-(phenylmethoxycarbonylamino)propyl]-1-[(4-methoxyphenyl)methyl]indol-2-yl]imidazol-4-yl]-2-[[2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-[[(E)-N'-nitrocarbamimidoyl]amino]pentanoyl]amino]acetyl]amino]propyl] 2,2-dimethylpropanoate 在 盐酸 、 lithium hydroxide 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(12S,15S,21S)-3-[(4-methoxyphenyl)methyl]-15-[3-[[(E)-N'-nitrocarbamimidoyl]amino]propyl]-13,16,19-trioxo-12-(phenylmethoxycarbonylamino)-1,3,14,17,20,24-hexazatetracyclo[21.2.1.02,10.04,9]hexacosa-2(10),4,6,8,23(26),24-hexaen-21-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  The Horner–Wadsworth–Emmons reaction in the synthesis of macrocyclic peptides: the Trp-His-Gly-Arg derived macrocycle of moroidin

  摘要：

  The Trp-His-Gly-Arg derived macrocycle 4 of moroidin 1 containing the unusual tryptophan C-2 histidine N-1 link has been synthesised in protected form. The key steps are displacement of a 2-chloroindole with a histidine derived nucleophile, a Horner-Wadsworth-Emmons reaction followed by asymmetric hydrogenation to establish the tryptophan side chain, and incorporation of the Gly-Arg dipeptide by peptide coupling. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01258-9
• 作为产物：
  描述：

  L-histidinol dihydrochloride 在 (R,R)-DlPAMP) rhodium(I) catalyst 盐酸 、 4-二甲氨基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 氢气 、 sodium hexamethyldisilazane 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 、 甲苯 、 乙腈 为溶剂， 20.0~80.0 ℃ 、517.11 kPa 条件下， 生成 [(2S)-3-[1-[3-[(2S)-3-methoxy-3-oxo-2-(phenylmethoxycarbonylamino)propyl]-1-[(4-methoxyphenyl)methyl]indol-2-yl]imidazol-4-yl]-2-[[2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-[[(E)-N'-nitrocarbamimidoyl]amino]pentanoyl]amino]acetyl]amino]propyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  The Horner–Wadsworth–Emmons reaction in the synthesis of macrocyclic peptides: the Trp-His-Gly-Arg derived macrocycle of moroidin

  摘要：

  The Trp-His-Gly-Arg derived macrocycle 4 of moroidin 1 containing the unusual tryptophan C-2 histidine N-1 link has been synthesised in protected form. The key steps are displacement of a 2-chloroindole with a histidine derived nucleophile, a Horner-Wadsworth-Emmons reaction followed by asymmetric hydrogenation to establish the tryptophan side chain, and incorporation of the Gly-Arg dipeptide by peptide coupling. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01258-9

文献信息

• The Horner–Wadsworth–Emmons reaction in the synthesis of macrocyclic peptides: the Trp-His-Gly-Arg derived macrocycle of moroidin
  作者：Justin R. Harrison、Christopher J. Moody

  DOI：10.1016/s0040-4039(03)01258-9

  日期：2003.7

  The Trp-His-Gly-Arg derived macrocycle 4 of moroidin 1 containing the unusual tryptophan C-2 histidine N-1 link has been synthesised in protected form. The key steps are displacement of a 2-chloroindole with a histidine derived nucleophile, a Horner-Wadsworth-Emmons reaction followed by asymmetric hydrogenation to establish the tryptophan side chain, and incorporation of the Gly-Arg dipeptide by peptide coupling. (C) 2003 Elsevier Science Ltd. All rights reserved.