2',3'-O-isopropylidene-5'-O-(2-(2-acetamido-4,6-benzylidene-2-deoxy-3-((R)-1-(methoxycarbonyl)ethoxy)-α-D-glucopyranosyl)acetamidosulfamoyl)uridine | 1065524-85-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',3'-O-isopropylidene-5'-O-(2-(2-acetamido-4,6-benzylidene-2-deoxy-3-((R)-1-(methoxycarbonyl)ethoxy)-α-D-glucopyranosyl)acetamidosulfamoyl)uridine
• CAS: 1065524-85-7
• 化学式: C₃₃H₄₂N₄O₁₆S
• 分子量: 782.78
• InChiKey: WFPLDZPZHQAOOH-MMWCGWQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.95
• 重原子数：
  54.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  247.34
• 氢给体数：
  3.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2',3'-O-isopropylidene-5'-O-(2-(2-acetamido-4,6-benzylidene-2-deoxy-3-((R)-1-(methoxycarbonyl)ethoxy)-α-D-glucopyranosyl)acetamidosulfamoyl)uridine 在 三氟乙酸 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis of 1-C-linked diphosphate analogues of UDP-N-Ac-glucosamine and UDP-N-Ac-muramic acid

  摘要：

  UDP-N-acetyl-glucosamine and UDP-N-acetyl-muramic acid are two important cytoplasmic precursors of bacterial peptidoglycan. The convergent synthesis of their analogues is reported. The alpha-1-C-linked-N-acetyl-glucosamine was synthesized using microwave-assisted Keck radical allylation. Oxidation of alkene derivatives to the corresponding carboxylic acids allowed attachment to O- and N-sulfamoyluridine giving stable diphosphate mimetics. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.009
• 作为产物：
  描述：

  2-(2-acetamido-4,6-O-benzylidene-2-deoxy-3-((R)-1-(methoxycarbonyl)ethoxy)-α-D-glucopyranosyl)acetic acid 、 2',3'-O-Isopropylidene-5'-O-sulfamoyluridine 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到2',3'-O-isopropylidene-5'-O-(2-(2-acetamido-4,6-benzylidene-2-deoxy-3-((R)-1-(methoxycarbonyl)ethoxy)-α-D-glucopyranosyl)acetamidosulfamoyl)uridine
  参考文献：
  名称：

  Synthesis of 1-C-linked diphosphate analogues of UDP-N-Ac-glucosamine and UDP-N-Ac-muramic acid

  摘要：

  UDP-N-acetyl-glucosamine and UDP-N-acetyl-muramic acid are two important cytoplasmic precursors of bacterial peptidoglycan. The convergent synthesis of their analogues is reported. The alpha-1-C-linked-N-acetyl-glucosamine was synthesized using microwave-assisted Keck radical allylation. Oxidation of alkene derivatives to the corresponding carboxylic acids allowed attachment to O- and N-sulfamoyluridine giving stable diphosphate mimetics. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.009