methyl (S)-2-(2-(R)-(2-acetamido-2-deoxy-4,6-di-O-acetyl-1-O-(uridine-5'-diphosphoryl)-3-α-D-glucopyranosyloxy)propanamido)propanoate 4-morpholino-N,N'-dicyclohexylcarboxamidine salt | 1093956-99-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: methyl (S)-2-(2-(R)-(2-acetamido-2-deoxy-4,6-di-O-acetyl-1-O-(uridine-5'-diphosphoryl)-3-α-D-glucopyranosyloxy)propanamido)propanoate 4-morpholino-N,N'-dicyclohexylcarboxamidine salt
• CAS: 1093956-99-0
• 化学式: C₁₇H₃₁N₃O*C₂₈H₄₂N₄O₂₂P₂
• 分子量: 1142.06
• InChiKey: RDKZOJFDPFDSMA-RRSKSWFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.49
• 重原子数：
  77.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  399.26
• 氢给体数：
  8.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-(2-(R)-(2-acetamido-2-deoxy-4,6-di-O-acetyl-1-O-(uridine-5'-diphosphoryl)-3-α-D-glucopyranosyloxy)propanamido)propanoate 4-morpholino-N,N'-dicyclohexylcarboxamidine salt 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以95%的产率得到trisodium (S)-2-(2-(R)-(2-acetamido-2-deoxy-4,6-di-O-acetyl-1-O-(uridine-5'-diphosphoryl)-3-α-D-glucopyranosyloxy)propanamido)propanoate
  参考文献：
  名称：

  Total synthesis of uridine diphosphate-N-acetylmuramoyl-l-alanine

  摘要：

  The first total synthesis of uridine diphosphate N-acetylmuramoyl-L-alanine in 13% overall yield is presented. The 11-step synthetic route is based on the synthetic strategy used for the synthesis Of Uridine diphosphate N-acetylmuramic acid, the MurC ligase Substrate. However, all unexpected amide bond cleavage under basic conditions demanded crucial modifications of the final synthetic steps. The total chemical synthesis Of MurD ligase substrate provides an excellent alternative to chemoenzymatic synthesis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.09.029
• 作为产物：
  描述：

  methyl (S)-2-(2-(R)-(2-acetamido-2-deoxy-4,6-di-O-acetyl-1-O-phosphoryl-3-α-D-glucopyranosyloxy)propanamido)propanoate triethylammonium salt 、 uridine-5-phosphomorpholidate 4-morpholine-N,N'-dicyclohexylcarboxamidine salt 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以61%的产率得到methyl (S)-2-(2-(R)-(2-acetamido-2-deoxy-4,6-di-O-acetyl-1-O-(uridine-5'-diphosphoryl)-3-α-D-glucopyranosyloxy)propanamido)propanoate 4-morpholino-N,N'-dicyclohexylcarboxamidine salt
  参考文献：
  名称：

  Total synthesis of uridine diphosphate-N-acetylmuramoyl-l-alanine

  摘要：

  The first total synthesis of uridine diphosphate N-acetylmuramoyl-L-alanine in 13% overall yield is presented. The 11-step synthetic route is based on the synthetic strategy used for the synthesis Of Uridine diphosphate N-acetylmuramic acid, the MurC ligase Substrate. However, all unexpected amide bond cleavage under basic conditions demanded crucial modifications of the final synthetic steps. The total chemical synthesis Of MurD ligase substrate provides an excellent alternative to chemoenzymatic synthesis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.09.029