N-((2R,3R,4R,5S,6R)-2-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-benzenesulfonamide | 144609-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((2R,3R,4R,5S,6R)-2-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-benzenesulfonamide
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-azido-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]benzenesulfonamide
• CAS: 144609-12-1
• 化学式: C₁₂H₁₆N₄O₆S
• 分子量: 344.348
• InChiKey: WEHVLDNMLQTKDI-LZQZFOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-((2R,3R,4R,5S,6R)-2-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-benzenesulfonamide 在 Raney-Ni (W-2) 吡啶 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(acetyl-benzenesulfonyl-amino)-6-amino-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  A stereoselective route from glycals to asparagine-linked N-protected glycopeptides

  摘要：

  Iodosulfonamidation of glycals followed by azidolysis produces anomerically pure 1beta-azido,2alpha-sulfonamidohexoses. Reduction of the azides, acylation of the resultant amines with an aspartic acid derivative, and deprotection of the 2-acetylamino function constitutes a completely stereospecific synthesis of asparagine-linked glycopeptide precursors from glycals.

  DOI：

  10.1021/jo00052a001
• 作为产物：
  描述：

  N-((2R,3R,4R,5R,6R)-2-Azido-4,5-bis-triethylsilanyloxy-6-triethylsilanyloxymethyl-tetrahydro-pyran-3-yl)-benzenesulfonamide 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 N-((2R,3R,4R,5S,6R)-2-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-benzenesulfonamide
  参考文献：
  名称：

  A stereoselective route from glycals to asparagine-linked N-protected glycopeptides

  摘要：

  Iodosulfonamidation of glycals followed by azidolysis produces anomerically pure 1beta-azido,2alpha-sulfonamidohexoses. Reduction of the azides, acylation of the resultant amines with an aspartic acid derivative, and deprotection of the 2-acetylamino function constitutes a completely stereospecific synthesis of asparagine-linked glycopeptide precursors from glycals.

  DOI：

  10.1021/jo00052a001

文献信息

• A stereoselective route from glycals to asparagine-linked N-protected glycopeptides
  作者：Frank E. McDonald、Samuel J. Danishefsky

  DOI：10.1021/jo00052a001

  日期：1992.12

  Iodosulfonamidation of glycals followed by azidolysis produces anomerically pure 1beta-azido,2alpha-sulfonamidohexoses. Reduction of the azides, acylation of the resultant amines with an aspartic acid derivative, and deprotection of the 2-acetylamino function constitutes a completely stereospecific synthesis of asparagine-linked glycopeptide precursors from glycals.