(1S,2R)-1-((2R,3R,4S,6S)-3-acetamido-4-(4-(4-(tert-butoxycarbonyl)piperazine-1-carbonyl)piperazin-1-yl)-6-hydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate | 1042129-75-8

• 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,6S)-3-acetamido-4-(4-(4-(tert-butoxycarbonyl)piperazine-1-carbonyl)piperazin-1-yl)-6-hydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate
• CAS: 1042129-75-8
• 化学式: C₃₂H₅₁N₅O₁₄
• 分子量: 729.782
• InChiKey: IKISABDMAWNVBP-UTRGJRIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.77
• 重原子数：
  51.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  220.09
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-((2R,3R,4S,6S)-3-acetamido-4-(4-(4-(tert-butoxycarbonyl)piperazine-1-carbonyl)piperazin-1-yl)-6-hydroxy-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95%的产率得到(1S,2R)-1-((2R,3R,4S,6S)-3-acetamido-6-hydroxy-6-(methoxycarbonyl)-4-(4-(piperazine-1-carbonyl)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
• 作为产物：
  描述：

  methyl (2S,4S,5R,6R)-5-acetamido-2-hydroxy-4-piperazin-1-yl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 、 三光气 、 N-Boc-哌嗪 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以202 mg的产率得到(1S,2R)-1-((2R,3R,4S,6S)-3-acetamido-4-(4-(4-(tert-butoxycarbonyl)piperazine-1-carbonyl)piperazin-1-yl)-6-hydroxy-6-(methoxycarbonyl)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