3-ethyl-1-phenyl-(3,5,6,7-tetra-O-acetyl-1,2-dideoxy-β-D-glycero-L-gluco-heptofurano<2,1-d>imidazolidin-2-one) | 148495-56-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-ethyl-1-phenyl-(3,5,6,7-tetra-O-acetyl-1,2-dideoxy-β-D-glycero-L-gluco-heptofurano<2,1-d>imidazolidin-2-one)
• 英文别名: [(2R,3S)-3-[(3aR,5R,6S,6aS)-6-acetyloxy-1-ethyl-2-oxo-3-phenyl-3a,5,6,6a-tetrahydrofuro[2,3-d]imidazol-5-yl]-2,3-diacetyloxypropyl] acetate
• CAS: 148495-56-1
• 化学式: C₂₄H₃₀N₂O₁₀
• 分子量: 506.51
• InChiKey: QEYHNWUGIUXVSI-DTILQVPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-ethyl-1-phenyl-(3,5,6,7-tetra-O-acetyl-1,2-dideoxy-β-D-glycero-L-gluco-heptofurano<2,1-d>imidazolidin-2-one) 在 sodium methylate 作用下， 以60%的产率得到3-ethyl-1-phenyl-1,2-dideoxy-β-D-glycero-L-gluco-heptofurano<2,1-d>imidazolidin-2-one
  参考文献：
  名称：

  On the mechanism of formation of glycofurano[2,1-d]-imidazolidin-2-ones. Reaction of 2-amino-2-deoxyheptopyranoses with isocyanates.

  摘要：

  Reaction of 2-aminosugars with isocyanates has been extended to other higher-carbon sugars. Ureido derivatives or, in most cases, monocyclic structures can be easily isolated. Importantly, the last substances display a relative trans disposition between the substituents at C-4 and C-5 of the heterocyclic ring, as a consequence of a rapid cis-trans isomerisation in acidic media. This stereochemical feature ensures (he stereocontrolled ring closure to give exclusively cis-fused glycofuranose systems. In the light of these results, some related reactions have been revised.

  DOI：

  10.1016/s0040-4020(01)86345-6
• 作为产物：
  描述：

  3-ethyl-1-phenyl-(3,5,6,7-tetra-O-acetyl-1,2-dideoxy-β-D-glycero-L-gluco-heptofurano<2,1-d>imidazolidin-2-thione) 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以16%的产率得到3-ethyl-1-phenyl-(3,5,6,7-tetra-O-acetyl-1,2-dideoxy-β-D-glycero-L-gluco-heptofurano<2,1-d>imidazolidin-2-one)
  参考文献：
  名称：

  On the mechanism of formation of glycofurano[2,1-d]-imidazolidin-2-ones. Reaction of 2-amino-2-deoxyheptopyranoses with isocyanates.

  摘要：

  Reaction of 2-aminosugars with isocyanates has been extended to other higher-carbon sugars. Ureido derivatives or, in most cases, monocyclic structures can be easily isolated. Importantly, the last substances display a relative trans disposition between the substituents at C-4 and C-5 of the heterocyclic ring, as a consequence of a rapid cis-trans isomerisation in acidic media. This stereochemical feature ensures (he stereocontrolled ring closure to give exclusively cis-fused glycofuranose systems. In the light of these results, some related reactions have been revised.

  DOI：

  10.1016/s0040-4020(01)86345-6