1,2-O-ethylidene-3,4,6-tri-O-[3-(N-methyl-N-benzyloxy-carbamoyl)-propyl]-α-D-galactopyranose | 1383567-50-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1,2-O-ethylidene-3,4,6-tri-O-[3-(N-methyl-N-benzyloxy-carbamoyl)-propyl]-α-D-galactopyranose
• CAS: 1383567-50-7
• 化学式: C₄₄H₅₉N₃O₁₂
• 分子量: 821.965
• InChiKey: RVULOUPNMKYBII-CKQMDFOLSA-N

物化性质

• 沸点：
  849.6±75.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  59.0
• 可旋转键数：
  25.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  144.0
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1,2-O-ethylidene-3,4,6-tri-O-[3-(N-methyl-N-benzyloxy-carbamoyl)-propyl]-α-D-galactopyranose 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以92%的产率得到1,2-O-ethylidene-3,4,6-tri-O-[3-(N-methyl-N-hydroxy-carbamoyl)-propyl]-α-D-galactopyranose
  参考文献：
  名称：

  Glycosiderophores: Synthesis of tris-hydroxamate siderophores based on a galactose or glycero central scaffold, Fe(III) complexation studies

  摘要：

  A series of five new hexadentate tris-hydroxamate ligands based on a D-galactose or a glycerol scaffold have been synthesized. Protonation and ferric complex formation constants have been determined from solution studies by potentiometric and spectrophotometric titrations. All ligands form 1:1 Fe:L complexes. The calculated pFe values at pH 7.4 span over the range 19.2-23.0 depending on the scaffold and on the length of the spacers between hydroxamate and central scaffold and on the N-methyl substitution. This new kind of artificial siderophores based on a glycoscaffold is of interest as it opens up an easy way to modulate the pFe. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2012.02.030
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 甲醇 、 sodium tetrahydroborate 、 lithium hydroxide monohydrate 、 sodium 、 四丁基碘化铵 、 sodium hydride 、 臭氧 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 3.5h， 生成 1,2-O-ethylidene-3,4,6-tri-O-[3-(N-methyl-N-benzyloxy-carbamoyl)-propyl]-α-D-galactopyranose
  参考文献：
  名称：

  Glycosiderophores: Synthesis of tris-hydroxamate siderophores based on a galactose or glycero central scaffold, Fe(III) complexation studies

  摘要：

  A series of five new hexadentate tris-hydroxamate ligands based on a D-galactose or a glycerol scaffold have been synthesized. Protonation and ferric complex formation constants have been determined from solution studies by potentiometric and spectrophotometric titrations. All ligands form 1:1 Fe:L complexes. The calculated pFe values at pH 7.4 span over the range 19.2-23.0 depending on the scaffold and on the length of the spacers between hydroxamate and central scaffold and on the N-methyl substitution. This new kind of artificial siderophores based on a glycoscaffold is of interest as it opens up an easy way to modulate the pFe. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2012.02.030