N-Acetyl-N-((2R,3R,4R,5S,6R)-2-azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-benzenesulfonamide | 144609-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-Acetyl-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]-N-(benzenesulfonyl)acetamide
• CAS: 144609-16-5
• 化学式: C₁₄H₁₈N₄O₇S
• 分子量: 386.386
• InChiKey: XZSGTKRWVOWKDX-DHGKCCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  26
• 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：
  147
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-Acetyl-N-((2R,3R,4R,5S,6R)-2-azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-benzenesulfonamide 在 platinum(IV) oxide 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-((S)-2-{(S)-3-[(2R,3R,4R,5S,6R)-3-(Acetyl-benzenesulfonyl-amino)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylcarbamoyl]-2-tert-butoxycarbonylamino-propionylamino}-3-methyl-butyrylamino)-3-tert-butoxy-propionic acid tert-butyl 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：

  3,4,6-tris-O-triethylsilyl-D-glucal 在 吡啶 、 甲醇 、 sodium azide 、 iodonium(di-γ-collidine) perchlorate 、 4 A molecular sieve 、 氨 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-Acetyl-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.