methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-((4-methyl phenoxy)thiocarbonyl)-8,9-O-isopropylidene-D-erythro-L-mannonononate | 170453-43-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-((4-methyl phenoxy)thiocarbonyl)-8,9-O-isopropylidene-D-erythro-L-mannonononate
• CAS: 170453-43-7
• 化学式: C₂₃H₃₁NO₉S
• 分子量: 497.566
• InChiKey: PRJXKKANTXXIAP-RFVXBFLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  121.78
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-((4-methyl phenoxy)thiocarbonyl)-8,9-O-isopropylidene-D-erythro-L-mannonononate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以53%的产率得到methyl 5-acetamido-2,6-anhydro-3,4,5-trideoxy-8,9-O-isopropylidene-D-erythro-L-mannonononate
  参考文献：
  名称：

  Synthesis of 4-epi-2-deoxy-2-Heq-N-acetylneuraminic acid and 2,4-dideoxy-2-HeqN-acetylneuraminic acid

  摘要：

  We have continued our work to develop novel analogues of sialic acid [1-4] that may specifically modulate the interaction between endogenous sialic acid and influenza virus haemagglutinin [3,5,6]. Functional groups of sialic acid that have been implicated for this virus-host recongnition are the glycerol side chain, N-acetyl group and the axially oriented carboxylic acid function [3]. In this report we describe the synthesis of two analogues, namely, 4-epi-2-deoxy-2-H-eq-N-acetylneuraminic acid (4-epi-2-d-2-H-eq-Neu5Ac) and 2,4-dideoxy-2-H-eq-N-acetylneuraminic acid (2,4-d(2)-2-H-eq-Neu5Ac).

  DOI：

  10.1016/0008-6215(95)00013-j
• 作为产物：
  描述：

  (2R,4S,5R,6R)-5-Acetylamino-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 作用下， 反应 1.0h， 生成 methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-((4-methyl phenoxy)thiocarbonyl)-8,9-O-isopropylidene-D-erythro-L-mannonononate
  参考文献：
  名称：

  Synthesis of 4-epi-2-deoxy-2-Heq-N-acetylneuraminic acid and 2,4-dideoxy-2-HeqN-acetylneuraminic acid

  摘要：

  We have continued our work to develop novel analogues of sialic acid [1-4] that may specifically modulate the interaction between endogenous sialic acid and influenza virus haemagglutinin [3,5,6]. Functional groups of sialic acid that have been implicated for this virus-host recongnition are the glycerol side chain, N-acetyl group and the axially oriented carboxylic acid function [3]. In this report we describe the synthesis of two analogues, namely, 4-epi-2-deoxy-2-H-eq-N-acetylneuraminic acid (4-epi-2-d-2-H-eq-Neu5Ac) and 2,4-dideoxy-2-H-eq-N-acetylneuraminic acid (2,4-d(2)-2-H-eq-Neu5Ac).

  DOI：

  10.1016/0008-6215(95)00013-j