methyl 4,5-bis-trimethylsilyloxy-pent-3-enoate | 617711-06-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 4,5-bis-trimethylsilyloxy-pent-3-enoate
• 英文别名: 4,5-bis-trimethylsilanyloxy-pent-3-enoic acid methyl ester；Methyl 4,5-bis(trimethylsilyloxy)pent-3-enoate；methyl 4,5-bis(trimethylsilyloxy)pent-3-enoate
• CAS: 617711-06-5
• 化学式: C₁₂H₂₆O₄Si₂
• 分子量: 290.507
• InChiKey: OCJBNXFSKHSSJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4,5-bis-trimethylsilyloxy-pent-3-enoate 、 methyl 5-azido-4,4-dimethoxypentanoate 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到
  参考文献：
  名称：

  Synthesis for the preparation of porphobilinogen, the compound as such as stabilized salt and intermediates thereof

  摘要：

  该发明涉及一种新的创新过程步骤序列，即索权项1中所述的步骤a）至e），用于制备卟啉原卟啉和中间体本身，作为重要的前体，例如式7的3-[4-甲氧羰甲基-5-(保护氨基甲基)-1H-吡咯-3-基]-丙酸甲酯，其中R是保护基，以及式8的3-[4-羧甲基-5-(保护氨基甲基)-1H-吡咯-3-基]-丙酸双碱金属盐，特别是式8a的3-[4-羧甲基-5-(苯乙酰氨基甲基)-1H-吡咯-3-基]-丙酸双锂盐，以及式9的羧酸酯4-(2-羧基乙基)-3-羧甲基-1H-吡咯-2-基-甲基铵，以及式9a的苯乙酸酯4-(2-羧基乙基)-3-羧甲基-1H-吡咯-2-基甲基铵，以及其用于制备卟啉原卟啉的用途。

  公开号：

  EP1357110A1
• 作为产物：
  描述：

  三甲基氯硅烷 、 5-hydroxy-4-oxopentanoic acid methyl ester 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以62.9%的产率得到methyl 4,5-bis-trimethylsilyloxy-pent-3-enoate
  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

• Synthesis for the preparation of porphobilinogen, the compound as such as stabilized salt and intermediates thereof
  申请人：Neier, Reinhard

  公开号：EP1357110A1

  公开（公告）日：2003-10-29

  The invention relates to a new inventive process sequence of steps a) to e) as claimed in Claim 1 for the preparation of porphobilinogen and intermediates per se as important precursors such as 3-[4-methoxycarbonylmethyl-5-(protected amino-methyl)-1 H-pyrrol-3-yl]-propionic acid methyl ester of formula 7 wherein R is a protective group, and 3-[4-Carboxymethyl-5-(protected amino-methyl)-1 H-pyrrol-3-yl]-propionic acid di-alkali metal salt of formula 8 and especially 3-[4-carboxymethyl-5-(phenylacetyl-amino-methyl)- 1H-pyrrol-3-yl]-propionic acid di-lithium salt of formula 8a and of carboxylate 4-(2-carboxy-ethyl)-3-carboxymethyl-1H-pyrrrol-2-yl-methyl-ammonium of formula 9 and of phenylacetate 4-(2-carboxy-ethyl)-3carboxymethyl-1 H-pyrrol-2-ylmethyl-ammonium of formula 9a and the use thereof for the preparation of porphobilinogen.

  该发明涉及一种新的创新过程步骤序列，即索权项1中所述的步骤a）至e），用于制备卟啉原卟啉和中间体本身，作为重要的前体，例如式7的3-[4-甲氧羰甲基-5-(保护氨基甲基)-1H-吡咯-3-基]-丙酸甲酯，其中R是保护基，以及式8的3-[4-羧甲基-5-(保护氨基甲基)-1H-吡咯-3-基]-丙酸双碱金属盐，特别是式8a的3-[4-羧甲基-5-(苯乙酰氨基甲基)-1H-吡咯-3-基]-丙酸双锂盐，以及式9的羧酸酯4-(2-羧基乙基)-3-羧甲基-1H-吡咯-2-基-甲基铵，以及式9a的苯乙酸酯4-(2-羧基乙基)-3-羧甲基-1H-吡咯-2-基甲基铵，以及其用于制备卟啉原卟啉的用途。
• 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.