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 | 1042129-77-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 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
• CAS: 1042129-77-0
• 化学式: C₄₅H₆₈N₆O₂₃
• 分子量: 1061.06
• InChiKey: XCPBVAHFQPMCOV-SHQKKJHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  74
• 可旋转键数：
  26
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  358
• 氢给体数：
  4
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  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 在 甲醇 、 sodium methylate 作用下， 反应 2.0h， 生成 (2S,4S,5R,6R)-5-acetamido-4-[4-[4-[(2S,4S,5R,6R)-5-acetamido-2-carboxy-2-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-4-yl]piperazine-1-carbonyl]piperazin-1-yl]-2-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
  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,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 、 (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 在 吡啶 作用下， 反应 24.0h， 以28%的产率得到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