N,N'-bis[(4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-O-allyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranos-2-y)l]urea | 1418181-44-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N'-bis[(4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-O-allyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranos-2-y)l]urea
• CAS: 1418181-44-8
• 化学式: C₈₉H₉₆N₂O₂₁
• 分子量: 1529.74
• InChiKey: PNHFDNFRCJWUFS-WUDFPXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.55
• 重原子数：
  112.0
• 可旋转键数：
  36.0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  223.83
• 氢给体数：
  0.0
• 氢受体数：
  21.0

反应信息

• 作为产物：
  描述：

  [(2R,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl] 2,2,2-trifluoro-N-phenylethanimidate 、 N,N'-bis(4-O-acetyl-1-O-allyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranos-2-yl)urea 在 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.75h， 以82%的产率得到N,N'-bis[(4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-O-allyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranos-2-y)l]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