2-deoxy-2-(3-phenylureido)-D-glycero-L-gluco-heptopyranose | 148405-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-deoxy-2-(3-phenylureido)-D-glycero-L-gluco-heptopyranose
• 英文别名: 1-[(2R,3S,4S,5R,6S)-6-[(1R)-1,2-dihydroxyethyl]-2,4,5-trihydroxyoxan-3-yl]-3-phenylurea
• CAS: 148405-15-6
• 化学式: C₁₄H₂₀N₂O₇
• 分子量: 328.322
• InChiKey: HBGOPVZBVGKZOP-ZEPSMKPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  152
• 氢给体数：
  7
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-(3-phenylureido)-D-glycero-L-gluco-heptopyranose 在 吡啶 作用下， 以 水 为溶剂， 反应 6.0h， 以68%的产率得到(4S,5S)-4-(D-galacto-pentitol-1-yl)-5-hydroxy-1-phenylimidazolidin-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：

  2-amino-2-deoxy-β-D-glycero-L-gluco-heptopyranose hydrochloride 、 异氰酸苯酯 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以75%的产率得到2-deoxy-2-(3-phenylureido)-D-glycero-L-gluco-heptopyranose
  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

文献信息

• On the mechanism of formation of glycofurano[2,1-d]-imidazolidin-2-ones. Reaction of 2-amino-2-deoxyheptopyranoses with isocyanates.
  作者：Martin Avalos、Reyes Babiano、Pedro Cintas、José L. Jiménez、Juan C. Palacios、Concepción Valencia

  DOI：10.1016/s0040-4020(01)86345-6

  日期：1993.3

  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.