6,6'-(N,N'-ethylene)-bis(D-glucaramid-1-oic acid)

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6'-(N,N'-ethylene)-bis(D-glucaramid-1-oic acid)
• 英文别名: (2R,3S,4S,5S)-6-[2-[[(2S,3S,4S,5R)-5-carboxy-2,3,4,5-tetrahydroxypentanoyl]amino]ethylamino]-2,3,4,5-tetrahydroxy-6-oxohexanoic acid
• 化学式: C₁₄H₂₄N₂O₁₄
• 分子量: 444.35
• InChiKey: RWIAATWHPCDRGB-CLDWMYACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  295
• 氢给体数：
  12
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  乙二胺 、 (2S)-2-[(2S,3R,4S)-3,4-二羟基-5-氧代四氢呋喃-2-基]-2-羟基乙酸 在 lithium acetate 作用下， 以 二甲基亚砜 为溶剂， 生成 6-[N-(2'-aminoethyl)]-D-glucaramide 、 、 、 6,6'-(N,N'-ethylene)-bis(D-glucaramid-1-oic acid)
  参考文献：
  名称：

  Alternating StereoregularHead,Tail–Tail,Head‐Poly(Alkylened‐Glucaramides) Derived from a Homologous Series of Symmetrical Diamido‐di‐d‐Glucaric Acid Monomers

  摘要：

  A method for the synthesis and purification of a homologous series of symmetrical diamido-diacids derived from D-glucaric acid and six alkylenediamines is described. Treating D-glucaro-6,3-lactone with an equimolar amount of lithium acetate dihydrate yielded lithium D-glucarate-6,3-lactone, which in turn was reacted with six alkylenediamines in dimethyl sulfoxide to give the target diamido-diacids. Six new alternating stereoregular polyamides, head, tail-tail, head-poly(alkylene D-glucaramides), were then synthesized by simple polycondensation reactions between the activated diamido-diacids [6,6'-(N,N'-alkylene)-bis(D-glucaramid-1-oic acid)s] and the alkylenediamines. Number average molecular weights for the polyamides were estimated by H-1 NMR end group analysis. Models for the three-dimensional shape of these alternating stereoregular polymers were produced from a combination of H-1 NMR data, molecular modeling studies performed on D-glucaramide, and crystal structures of various acyclic D-glucaric acid derivatives.

  DOI：

  10.1081/car-120020482

文献信息

• Alternating Stereoregular<i>Head</i>,<i>Tail</i>–<i>Tail</i>,<i>Head</i>‐Poly(Alkylene<scp>d</scp>‐Glucaramides) Derived from a Homologous Series of Symmetrical Diamido‐di‐<scp>d</scp>‐Glucaric Acid Monomers
  作者：Susan D. Styron、Donald E. Kiely、Glenn Ponder

  DOI：10.1081/car-120020482

  日期：2003.1.5

  A method for the synthesis and purification of a homologous series of symmetrical diamido-diacids derived from D-glucaric acid and six alkylenediamines is described. Treating D-glucaro-6,3-lactone with an equimolar amount of lithium acetate dihydrate yielded lithium D-glucarate-6,3-lactone, which in turn was reacted with six alkylenediamines in dimethyl sulfoxide to give the target diamido-diacids. Six new alternating stereoregular polyamides, head, tail-tail, head-poly(alkylene D-glucaramides), were then synthesized by simple polycondensation reactions between the activated diamido-diacids [6,6'-(N,N'-alkylene)-bis(D-glucaramid-1-oic acid)s] and the alkylenediamines. Number average molecular weights for the polyamides were estimated by H-1 NMR end group analysis. Models for the three-dimensional shape of these alternating stereoregular polymers were produced from a combination of H-1 NMR data, molecular modeling studies performed on D-glucaramide, and crystal structures of various acyclic D-glucaric acid derivatives.