(E)-4-(2,3-Bis-benzyloxy-benzoylamino)-but-2-enoic acid 2-[{2-[(E)-4-(2,3-bis-benzyloxy-benzoylamino)-but-2-enoyloxy]-ethyl}-(2-hydroxy-ethyl)-amino]-ethyl ester | 909704-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-(2,3-Bis-benzyloxy-benzoylamino)-but-2-enoic acid 2-[{2-[(E)-4-(2,3-bis-benzyloxy-benzoylamino)-but-2-enoyloxy]-ethyl}-(2-hydroxy-ethyl)-amino]-ethyl ester
• CAS: 909704-35-4
• 化学式: C₅₆H₅₇N₃O₁₁
• 分子量: 948.082
• InChiKey: ZUKUXGGLYWLROR-CMNXJCJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.66
• 重原子数：
  70.0
• 可旋转键数：
  28.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  171.19
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (E)-4-(2,3-Bis-benzyloxy-benzoylamino)-but-2-enoic acid 2-[{2-[(E)-4-(2,3-bis-benzyloxy-benzoylamino)-but-2-enoyloxy]-ethyl}-(2-hydroxy-ethyl)-amino]-ethyl ester 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成 2-Hydroxy-benzoic acid 2-(bis-{2-[4-(2,3-dihydroxy-benzoylamino)-butyryloxy]-ethyl}-amino)-ethyl ester
  参考文献：
  名称：

  Conjugates of methyl 6-aminopenicillanate with biscatechol-hydroxamate chelators: synthesis and siderophoric activity

  摘要：

  A synthesis of biscatechol-hydroxamate and triscatechol chelators and of conjugates of the former with methyl 6-aminopenicillanate is described. It is based on the multiple use of the ylide Ph3PCCO as a C-2 building block in one-pot coupling reactions between aldehydes and alcohols or amines. These conjugates were actively internalized into siderophore-deficient Escherichia coli mutant H5596. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.056
• 作为产物：
  描述：

  (E)-4-(2,3-Bis-benzyloxy-benzoylamino)-but-2-enoic acid 2-{{2-[(E)-4-(2,3-bis-benzyloxy-benzoylamino)-but-2-enoyloxy]-ethyl}-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-amino}-ethyl ester 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以76%的产率得到(E)-4-(2,3-Bis-benzyloxy-benzoylamino)-but-2-enoic acid 2-[{2-[(E)-4-(2,3-bis-benzyloxy-benzoylamino)-but-2-enoyloxy]-ethyl}-(2-hydroxy-ethyl)-amino]-ethyl ester
  参考文献：
  名称：

  Conjugates of methyl 6-aminopenicillanate with biscatechol-hydroxamate chelators: synthesis and siderophoric activity

  摘要：

  A synthesis of biscatechol-hydroxamate and triscatechol chelators and of conjugates of the former with methyl 6-aminopenicillanate is described. It is based on the multiple use of the ylide Ph3PCCO as a C-2 building block in one-pot coupling reactions between aldehydes and alcohols or amines. These conjugates were actively internalized into siderophore-deficient Escherichia coli mutant H5596. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.056