methyl (2S,4S,5R,6R)-5-acetamido-2-hydroxy-4-piperazin-1-yl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate | 1042129-73-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,4S,5R,6R)-5-acetamido-2-hydroxy-4-piperazin-1-yl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 1042129-73-6
• 化学式: C₂₂H₃₅N₃O₁₁
• 分子量: 517.533
• InChiKey: SGRWEQOJQHXESS-QDRUEPRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  179
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  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 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2S,4S,5R,6R)-5-acetamido-4-[4-[4-[(2S,4S,5R,6R)-5-acetamido-2-hydroxy-2-methoxycarbonyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxan-4-yl]piperazine-1-carbonyl]piperazin-1-yl]-2-hydroxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  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：

  tert-butyl 4-[(2S,4S,5R,6R)-5-acetamido-2-hydroxy-2-methoxycarbonyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxan-4-yl]piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl (2S,4S,5R,6R)-5-acetamido-2-hydroxy-4-piperazin-1-yl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  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