(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-6-acetoxy-6-(methoxycarbonyl)-4-(piperazin-1-yl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate | 1042129-80-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-6-acetoxy-6-(methoxycarbonyl)-4-(piperazin-1-yl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate
• CAS: 1042129-80-5
• 化学式: C₂₄H₃₇N₃O₁₂
• 分子量: 559.571
• InChiKey: DQRHHYCABQQTEM-LPDXNUGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.59
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  185.1
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-6-acetoxy-6-(methoxycarbonyl)-4-(piperazin-1-yl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 、 1,3-二溴丙烷 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 以71%的产率得到
  参考文献：
  名称：

  Simultaneous 2-O-deacetylation and 4-amination of peracetylated Neu5Ac: application to the synthesis of (4→4)-piperazine derivatives linked sialic acid dimers

  摘要：

  A simultaneous stereoselective 2-O-deacetylation and 4-amination reaction of peracetylated Neu5Ac 1 has been established with cyclic secondary amines, such as 1-N-Boc-piperazine. Four C-2-symmetric and two asymmetric sialic acid dimers with (4 -> 4)-piperazine derivatives linked were synthesized. They may serve as precursors of unnatural polysialic acids. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.046
• 作为产物：
  描述：

  (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-6-acetoxy-4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以97%的产率得到(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-6-acetoxy-6-(methoxycarbonyl)-4-(piperazin-1-yl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate
  参考文献：
  名称：

  Simultaneous 2-O-deacetylation and 4-amination of peracetylated Neu5Ac: application to the synthesis of (4→4)-piperazine derivatives linked sialic acid dimers

  摘要：

  A simultaneous stereoselective 2-O-deacetylation and 4-amination reaction of peracetylated Neu5Ac 1 has been established with cyclic secondary amines, such as 1-N-Boc-piperazine. Four C-2-symmetric and two asymmetric sialic acid dimers with (4 -> 4)-piperazine derivatives linked were synthesized. They may serve as precursors of unnatural polysialic acids. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.046