6-[N-(10'-aminodecyl)]-D-glucaramide, sodium salt

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-[N-(10'-aminodecyl)]-D-glucaramide, sodium salt
• 英文别名: sodium;(2S,3S,4S,5R)-N-(10-aminodecyl)-2,3,4,5,6-pentahydroxy-6-oxohexanimidate
• 化学式: C₁₆H₃₁N₂O₇*Na
• 分子量: 386.421
• InChiKey: XRUJCRBPAIMOKB-YXCQRQMQSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.64
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  180
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲醇 、 6-[N-(10'-aminodecyl)]-D-glucaramide, sodium salt 在 乙酰氯 作用下， 反应 3.0h， 生成 (S)-N-(10-Amino-decyl)-2-((2S,3R,4R)-3,4-dihydroxy-5-oxo-tetrahydro-furan-2-yl)-2-hydroxy-acetamide; hydrochloride 、
  参考文献：
  名称：

  Synthesis of Stereoregular Head,Tail Hydroxylated Nylons Derived from d-Glucose

  摘要：

  A simple procedure for the preparation of stereoregular polyhydroxypolyamides, i.e., head,tail hydroxylated nylons, derived from D-glucaric acid and alkylenediamines is described. Sodium D-glucarate 6,3-lactone was made in two steps from monopotassium D-glucarate by way of D-glucaro-6,3-lactone. Methanol insoluble salt of sodium 6-[N-(aminoalkyl)]-D-glucaramide monomer precursors were conveniently prepared by refluxing methanol solutions of even-numbered C-2 to C-12 aliphatic diamines with insoluble sodium D-glucarate-6,3-lactone. Each of the resulting salts was esterified/lactonized at the C-1 carboxylate terminus with HCl/methanol, and the products were made basic to give the corresponding free base amino acid ester/lactone mixture. The latter spontaneously underwent self-polymerization to give the target polyamides. An important feature of this general procedure for stereoregular polyamides from chiral D-glucaric acid is that it does not require any carbohydrate hydroxyl group protection/deprotection steps.

  DOI：

  10.1021/jo960201e
• 作为产物：
  描述：

  monopotassium D-glucarate 在 H⁽¹⁺⁾ resin Rexyn 100(H) 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 6-[N-(10'-aminodecyl)]-D-glucaramide, sodium salt
  参考文献：
  名称：

  Synthesis of Stereoregular Head,Tail Hydroxylated Nylons Derived from d-Glucose

  摘要：

  A simple procedure for the preparation of stereoregular polyhydroxypolyamides, i.e., head,tail hydroxylated nylons, derived from D-glucaric acid and alkylenediamines is described. Sodium D-glucarate 6,3-lactone was made in two steps from monopotassium D-glucarate by way of D-glucaro-6,3-lactone. Methanol insoluble salt of sodium 6-[N-(aminoalkyl)]-D-glucaramide monomer precursors were conveniently prepared by refluxing methanol solutions of even-numbered C-2 to C-12 aliphatic diamines with insoluble sodium D-glucarate-6,3-lactone. Each of the resulting salts was esterified/lactonized at the C-1 carboxylate terminus with HCl/methanol, and the products were made basic to give the corresponding free base amino acid ester/lactone mixture. The latter spontaneously underwent self-polymerization to give the target polyamides. An important feature of this general procedure for stereoregular polyamides from chiral D-glucaric acid is that it does not require any carbohydrate hydroxyl group protection/deprotection steps.

  DOI：

  10.1021/jo960201e

文献信息

• Synthesis of Stereoregular <i>Head</i>,<i>Tail</i> Hydroxylated Nylons Derived from <scp>d</scp>-Glucose
  作者：Liang Chen、Donald E. Kiely

  DOI：10.1021/jo960201e

  日期：1996.1.1

  A simple procedure for the preparation of stereoregular polyhydroxypolyamides, i.e., head,tail hydroxylated nylons, derived from D-glucaric acid and alkylenediamines is described. Sodium D-glucarate 6,3-lactone was made in two steps from monopotassium D-glucarate by way of D-glucaro-6,3-lactone. Methanol insoluble salt of sodium 6-[N-(aminoalkyl)]-D-glucaramide monomer precursors were conveniently prepared by refluxing methanol solutions of even-numbered C-2 to C-12 aliphatic diamines with insoluble sodium D-glucarate-6,3-lactone. Each of the resulting salts was esterified/lactonized at the C-1 carboxylate terminus with HCl/methanol, and the products were made basic to give the corresponding free base amino acid ester/lactone mixture. The latter spontaneously underwent self-polymerization to give the target polyamides. An important feature of this general procedure for stereoregular polyamides from chiral D-glucaric acid is that it does not require any carbohydrate hydroxyl group protection/deprotection steps.