1-(2-aminoethylamino)-1-deoxy-D-galactitol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-aminoethylamino)-1-deoxy-D-galactitol
• 英文别名: (2R,3S,4R,5S)-6-((2-Aminoethyl)amino)hexane-1,2,3,4,5-pentaol；(2R,3S,4R,5S)-6-(2-aminoethylamino)hexane-1,2,3,4,5-pentol
• 化学式: C₈H₂₀N₂O₅
• 分子量: 224.257
• InChiKey: IYGXXJPSPOMELO-OSMVPFSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.03
• 重原子数：
  15.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  139.2
• 氢给体数：
  7.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  溴乙酸 、 1-(2-aminoethylamino)-1-deoxy-D-galactitol 在 lithium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 以43%的产率得到1-deoxy-1-(2-aminoethylamino)-D-galacticol-N-triacetate
  参考文献：
  名称：

  Reductive amination of aldohexoses with mono- and bifunctional alkyl amines: conversion of carbohydrates into EDTA type complexing agents

  摘要：

  It is shown by H-1 and C-13 NMR spectroscopy (1D and 2D) that beta-N-propylgalactosylamine (5a) is the major species present in an equimolar aqueous solution of D-galactose (1a) and propylamine (PA). In equimolar solutions of aldohexoses (1a-c) and ethylenediamine (EN) or 1,3-diaminopropane (DAP) in addition to mono- (9) and diglycosylamines (12) tetra-imidazole (8, n=1) and hexahydropyrimidine derivatives (8, n=2), respectively, are formed. Hydrogenation of equimolar solutions of aldohexoses (1a-c) and primary amines (PA, EN, and DAP) at 100 atm. and 50 degrees C, using 5% Pt on carbon as the catalyst, gave amino sugars 13-16 in good yields. Carboxymethylation of 14a-b resulted in sugar based EDTA type complexing agents (17a-b) with promising chelating abilities towards Cd(II) and Ca(II) at high pH.

  DOI：

  10.1016/s0040-4020(01)85293-5
• 作为产物：
  描述：

  D-吡喃葡萄糖 、 乙二胺 在 platinum on activated charcoal 氢气 作用下， 以 水 为溶剂， 50.0 ℃ 、10.13 MPa 条件下， 反应 12.0h， 以75%的产率得到1-(2-aminoethylamino)-1-deoxy-D-galactitol
  参考文献：
  名称：

  Reductive amination of aldohexoses with mono- and bifunctional alkyl amines: conversion of carbohydrates into EDTA type complexing agents

  摘要：

  It is shown by H-1 and C-13 NMR spectroscopy (1D and 2D) that beta-N-propylgalactosylamine (5a) is the major species present in an equimolar aqueous solution of D-galactose (1a) and propylamine (PA). In equimolar solutions of aldohexoses (1a-c) and ethylenediamine (EN) or 1,3-diaminopropane (DAP) in addition to mono- (9) and diglycosylamines (12) tetra-imidazole (8, n=1) and hexahydropyrimidine derivatives (8, n=2), respectively, are formed. Hydrogenation of equimolar solutions of aldohexoses (1a-c) and primary amines (PA, EN, and DAP) at 100 atm. and 50 degrees C, using 5% Pt on carbon as the catalyst, gave amino sugars 13-16 in good yields. Carboxymethylation of 14a-b resulted in sugar based EDTA type complexing agents (17a-b) with promising chelating abilities towards Cd(II) and Ca(II) at high pH.

  DOI：

  10.1016/s0040-4020(01)85293-5