2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl fluoride | 187330-17-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl fluoride
• CAS: 187330-17-2
• 化学式: C₁₅H₁₅ClFN₃O₅
• 分子量: 371.753
• InChiKey: AJHSGLVEPWRYCR-UKHFBKCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  102.75
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl fluoride 在 二氯二茂锆 、 4 A molecular sieve 、 四丁基溴化铵 、 silver trifluoromethanesulfonate 、 silver perchlorate 、 硫脲 、 copper(ll) bromide 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.75h， 生成
  参考文献：
  名称：

  A new strategy for stereoselective synthesis of sialic acid-containing glycopeptide fragment

  摘要：

  Sialic acid donor 5, which has a thiophenyl group as a stereocontrolling auxiliary and thiomethyl group as a leaving group was prepared and subjected to model glycosylation. Reactions with acceptor substrates 6, 7, and 8 gave coupled products 9b, 10b, and 11b, respectively, in a higher efficiency than previously observed for the bromide la. This reaction was further applied to the synthesis of protected glyco-amino acid fragment 12, that is strategically designed for the synthesis of sialic acid containing glycopeptides. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00172-1
• 作为产物：
  描述：

  (2S,4aR,7R,8R,8aR)-7-Azido-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 、 氯乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以52%的产率得到2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl fluoride
  参考文献：
  名称：

  A new strategy for stereoselective synthesis of sialic acid-containing glycopeptide fragment

  摘要：

  Sialic acid donor 5, which has a thiophenyl group as a stereocontrolling auxiliary and thiomethyl group as a leaving group was prepared and subjected to model glycosylation. Reactions with acceptor substrates 6, 7, and 8 gave coupled products 9b, 10b, and 11b, respectively, in a higher efficiency than previously observed for the bromide la. This reaction was further applied to the synthesis of protected glyco-amino acid fragment 12, that is strategically designed for the synthesis of sialic acid containing glycopeptides. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00172-1