methyl (S)-2-(2-(R)-(2-acetamido-4,6-di-O-acetyl-1-O-benzyl-2-deoxy-3-α-D-glucopyranosyloxy)propanamido)propanoate | 1093956-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (S)-2-(2-(R)-(2-acetamido-4,6-di-O-acetyl-1-O-benzyl-2-deoxy-3-α-D-glucopyranosyloxy)propanamido)propanoate
• 英文别名: methyl (2S)-2-[[(2R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-3-acetyloxy-2-(acetyloxymethyl)-6-phenylmethoxyoxan-4-yl]oxypropanoyl]amino]propanoate
• CAS: 1093956-89-8
• 化学式: C₂₆H₃₆N₂O₁₁
• 分子量: 552.579
• InChiKey: ODBURUGGYSCBRF-KSGVNOMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  165
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-(2-(R)-(2-acetamido-4,6-di-O-acetyl-1-O-benzyl-2-deoxy-3-α-D-glucopyranosyloxy)propanamido)propanoate 在 10% Pd/C 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以98%的产率得到methyl (S)-2-(2-(R)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-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：

  乙酸酐 、 N-<2-O-(benzyl 2-acetamido-2,3-dideoxy-α-D-glucopyranoside-3-yl)-D-lactoyl>-L-alanine methyl ester 在 吡啶 作用下， 反应 12.0h， 以1.78 g的产率得到methyl (S)-2-(2-(R)-(2-acetamido-4,6-di-O-acetyl-1-O-benzyl-2-deoxy-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