1-amino-1-deoxy-2,3,4,5-tetra-O-methyl-D-sorbitol | 1314518-50-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-amino-1-deoxy-2,3,4,5-tetra-O-methyl-D-sorbitol
• 英文别名: (2R,3R,4R,5S)-6-amino-2,3,4,5-tetramethoxyhexan-1-ol
• CAS: 1314518-50-7
• 化学式: C₁₀H₂₃NO₅
• 分子量: 237.296
• InChiKey: IPUGAHBJEODVNC-SGIHWFKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-amino-1-deoxy-2,3,4,5-tetra-O-methyl-D-sorbitol 在 zirconium acetylacetonate 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 18.0h， 生成 1,3-bis[(2S,3R,4R,5R)-6-hydroxy-2,3,4,5-tetramethoxyhexyl]urea
  参考文献：
  名称：

  Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer

  摘要：

  Aminoalditol 1-amino-1-deoxy-D-sorbitol (1) was readily converted into 2,3,4,5-tetra-O-methyl derivative 5, a key precursor of a sugar-based [n]-polyurethane. For the polymerization, the free amino or primary hydroxyl groups of 5 were selectively activated and employed as starting monomers in two alternative procedures. Thus, the amino function of 5 was converted into the isocyanate derivative by treatment with di-tert-butyltricarbonate, and polymerized in situ in the presence of Zr(IV) acetylacetonate. The resulting poly(1-amino-1-deoxy-2,3,4,5-tetra-O-methyl-D-sorbitol)urethane (8) had a moderate molecular weight and showed the presence of urea units. The alternative synthesis of 8 involved the activation of the free hydroxyl group of 5 as the corresponding phenylcarbonate. The polymerization of this alpha-amino-omega-phenylcarbonate alditol monomer does not require a metal catalyst. The resulting material exhibited an improved molecular weight and higher purity than that obtained via the isocyanate. [n]-polyurethane 8 was highly soluble in water as well as in common organic solvents (chloroform, acetone, ethyl acetate, etc) and was obtained as an amorphous material which was characterized thermally and spectroscopically. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.02.022
• 作为产物：
  描述：

  1-deoxy-2,3,4,5-tetra-O-methyl-6-O-trityl-1-N-tritylamino-D-sorbitol 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 以93%的产率得到1-amino-1-deoxy-2,3,4,5-tetra-O-methyl-D-sorbitol
  参考文献：
  名称：

  Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer

  摘要：

  Aminoalditol 1-amino-1-deoxy-D-sorbitol (1) was readily converted into 2,3,4,5-tetra-O-methyl derivative 5, a key precursor of a sugar-based [n]-polyurethane. For the polymerization, the free amino or primary hydroxyl groups of 5 were selectively activated and employed as starting monomers in two alternative procedures. Thus, the amino function of 5 was converted into the isocyanate derivative by treatment with di-tert-butyltricarbonate, and polymerized in situ in the presence of Zr(IV) acetylacetonate. The resulting poly(1-amino-1-deoxy-2,3,4,5-tetra-O-methyl-D-sorbitol)urethane (8) had a moderate molecular weight and showed the presence of urea units. The alternative synthesis of 8 involved the activation of the free hydroxyl group of 5 as the corresponding phenylcarbonate. The polymerization of this alpha-amino-omega-phenylcarbonate alditol monomer does not require a metal catalyst. The resulting material exhibited an improved molecular weight and higher purity than that obtained via the isocyanate. [n]-polyurethane 8 was highly soluble in water as well as in common organic solvents (chloroform, acetone, ethyl acetate, etc) and was obtained as an amorphous material which was characterized thermally and spectroscopically. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.02.022

文献信息

• Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer
  作者：Adriana A. Kolender、Silvina M. Arce、Oscar Varela

  DOI：10.1016/j.carres.2011.02.022

  日期：2011.9

  Aminoalditol 1-amino-1-deoxy-D-sorbitol (1) was readily converted into 2,3,4,5-tetra-O-methyl derivative 5, a key precursor of a sugar-based [n]-polyurethane. For the polymerization, the free amino or primary hydroxyl groups of 5 were selectively activated and employed as starting monomers in two alternative procedures. Thus, the amino function of 5 was converted into the isocyanate derivative by treatment with di-tert-butyltricarbonate, and polymerized in situ in the presence of Zr(IV) acetylacetonate. The resulting poly(1-amino-1-deoxy-2,3,4,5-tetra-O-methyl-D-sorbitol)urethane (8) had a moderate molecular weight and showed the presence of urea units. The alternative synthesis of 8 involved the activation of the free hydroxyl group of 5 as the corresponding phenylcarbonate. The polymerization of this alpha-amino-omega-phenylcarbonate alditol monomer does not require a metal catalyst. The resulting material exhibited an improved molecular weight and higher purity than that obtained via the isocyanate. [n]-polyurethane 8 was highly soluble in water as well as in common organic solvents (chloroform, acetone, ethyl acetate, etc) and was obtained as an amorphous material which was characterized thermally and spectroscopically. (C) 2011 Elsevier Ltd. All rights reserved.