methyl 3-[4-(2-methoxy-2-oxoethyl)-5-[[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]methyl]-1H-pyrrol-3-yl]propanoate | 1006610-18-9

• 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: methyl 3-[4-(2-methoxy-2-oxoethyl)-5-[[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]methyl]-1H-pyrrol-3-yl]propanoate
• CAS: 1006610-18-9
• 化学式: C₂₆H₃₅N₃O₇
• 分子量: 501.58
• InChiKey: XPCPXVQZFXAXMQ-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-[4-(2-methoxy-2-oxoethyl)-5-[[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]methyl]-1H-pyrrol-3-yl]propanoate 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl 3-[5-[[[(2S)-2-amino-3-phenylpropanoyl]amino]methyl]-4-(2-methoxy-2-oxoethyl)-1H-pyrrol-3-yl]propanoate;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Facile Synthesis of a “Ready to Use” Precursor of Porphobilinogen and Its Amino Acid Derivatives

  摘要：

  [GRAPHICS]A practical synthesis of porphobilinogen based on the biosynthetic mechanism is described. The crossed Mukayiama. aldol reaction is the key step creating the central carbon-carbon bond between the two protected forms of 5-aminolevulinic acids. The optimized sequence gives a crystalline, storable precursor, which can be transformed in high yield into porphobilinogen and bioconjugates thereof. The enzymatic hydrolysis of the precursor produces porphobilinogen in quantitative yield.

  DOI：

  10.1021/jo702319n
• 作为产物：
  描述：

  dimethyl 3-(2-azidoacetyl)-4-azidomethyl-4-methoxyheptanedioate 、 Boc-Phe-OPfp 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、413.69 kPa 条件下， 反应 24.0h， 生成 methyl 3-[4-(2-methoxy-2-oxoethyl)-5-[[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]methyl]-1H-pyrrol-3-yl]propanoate
  参考文献：
  名称：

  Facile Synthesis of a “Ready to Use” Precursor of Porphobilinogen and Its Amino Acid Derivatives

  摘要：

  [GRAPHICS]A practical synthesis of porphobilinogen based on the biosynthetic mechanism is described. The crossed Mukayiama. aldol reaction is the key step creating the central carbon-carbon bond between the two protected forms of 5-aminolevulinic acids. The optimized sequence gives a crystalline, storable precursor, which can be transformed in high yield into porphobilinogen and bioconjugates thereof. The enzymatic hydrolysis of the precursor produces porphobilinogen in quantitative yield.

  DOI：

  10.1021/jo702319n

文献信息

• Facile Synthesis of a “Ready to Use” Precursor of Porphobilinogen and Its Amino Acid Derivatives
  作者：Carole Pissot Soldermann、Ramakrishnan Vallinayagam、Manuel Tzouros、Reinhard Neier

  DOI：10.1021/jo702319n

  日期：2008.1.1

  [GRAPHICS]A practical synthesis of porphobilinogen based on the biosynthetic mechanism is described. The crossed Mukayiama. aldol reaction is the key step creating the central carbon-carbon bond between the two protected forms of 5-aminolevulinic acids. The optimized sequence gives a crystalline, storable precursor, which can be transformed in high yield into porphobilinogen and bioconjugates thereof. The enzymatic hydrolysis of the precursor produces porphobilinogen in quantitative yield.