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 | 943982-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 943982-38-5
• 化学式: C₂₇H₄₃N₃O₁₃
• 分子量: 617.651
• InChiKey: AYNJPMCIMGBWLY-UAVGPPOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  197
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (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 、 N-Boc-哌嗪 在 吡啶 作用下， 反应 24.0h， 以80%的产率得到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
  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

文献信息

• Simultaneous stereoselective 4-amination with cyclic secondary amines and 2-O-deacetylation of peracetylated sialic acid derivatives
  作者：Deju Ye、Jian Li、Jian Zhang、Hong Liu、Hualiang Jiang

  DOI：10.1016/j.tetlet.2007.04.023

  日期：2007.6

  Treatment of methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-beta-L-glycero-D-galacto-2-nonulopyranosidonate (1) with cyclic secondary amines in pyridine at room temperature for 24 h afforded unusual products (2a-g). Related experiments were carried out to explain the formation of 4-amination and 2-O-deacetylation of peracetylated sialic acid derivatives (2a-g). This reaction may provide a new strategy for the preparation of Zanamivir analogues as neuraminidase inhibitors for anti-H5N1 subtype of avian influenza virus (AIV). (c) 2007 Elsevier Ltd. All rights reserved.