N,N'-bis(1-O-allyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranos-2-yl)urea | 1418181-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: N,N'-bis(1-O-allyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranos-2-yl)urea
• CAS: 1418181-45-9
• 化学式: C₃₃H₄₀N₂O₁₁
• 分子量: 640.687
• InChiKey: GADAUNOAYZPSFK-FFZGYWJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  155.43
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N,N'-bis(1-O-allyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranos-2-yl)urea 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 7.0h， 以61%的产率得到N,N'-bis(1-O-allyl-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-galactopyranos-2-yl)urea
  参考文献：
  名称：

  Versatile and self-assembling urea-linked neosaccharides from sugar aminoalcohols

  摘要：

  The increasing interest in urea compounds as self-assembling molecules, ion transporters and organo-catalysts prompted several efforts towards synthetic urea-linked glycomimetics. In this frame we studied in details a novel two steps dimerization reaction of sugar vicinal aminoalcohol building blocks, opening a synthetic path to a series of urea-linked neosaccharides. Glucosamine neodisaccharide possessing an oxazolidinone-urea-oxazolidinone system could be transformed into both cyclic and higher linear neosaccharides. Furthermore, a series of six urea-linked glucosamine and galactosamine neodisaccharides was tested for self-assembling properties by measuring NMR spectra at different temperatures and concentrations as well as by gelation of several organic solvents. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.005
• 作为产物：
  描述：

  (2S,4aR,6S,7R,8R,8aR)-6-(allyloxy)-7-amino-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-ol 在 sodium hydride 、 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 49.25h， 生成 N,N'-bis(1-O-allyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranos-2-yl)urea
  参考文献：
  名称：

  Versatile and self-assembling urea-linked neosaccharides from sugar aminoalcohols

  摘要：

  The increasing interest in urea compounds as self-assembling molecules, ion transporters and organo-catalysts prompted several efforts towards synthetic urea-linked glycomimetics. In this frame we studied in details a novel two steps dimerization reaction of sugar vicinal aminoalcohol building blocks, opening a synthetic path to a series of urea-linked neosaccharides. Glucosamine neodisaccharide possessing an oxazolidinone-urea-oxazolidinone system could be transformed into both cyclic and higher linear neosaccharides. Furthermore, a series of six urea-linked glucosamine and galactosamine neodisaccharides was tested for self-assembling properties by measuring NMR spectra at different temperatures and concentrations as well as by gelation of several organic solvents. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.005