8-azidooctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 1002744-48-0

• 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: 8-azidooctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS: 1002744-48-0
• 化学式: C₂₃H₃₄N₄O₆
• 分子量: 462.546
• InChiKey: ZNLRTDZGSKMAMM-YTAOHXRWSA-N

反应信息

• 作为反应物：
  描述：

  8-azidooctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 、 在 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以65%的产率得到8-azidooctyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosil-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the ‘primer–adaptor’ trisaccharide moiety of Escherichia coli O8, O9, and O9a lipopolysaccharide

  摘要：

  Described is the synthesis of the trisaccharide alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->3)-beta-D-GlcpNAcO(CH2)(8)N-3, the glycan portion of which corresponds to the 'adaptor-primer' moiety linking the O-chain and core oligosaccharide in the lipopolysaccharide of several Escherichia coli and Klebsiella pneumoniae serotypes. This report represents the first synthesis of this trisaccharide motif, and in the route involved, a key step is a [2+1] coupling of a protected Manp-(1-->3)-alpha-D-Manp glycosyl donor with a GlcpNAc acceptor. The azido group was included in the target to facilitate future preparation of neoglycoconjugates. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.08.020
• 作为产物：
  描述：

  8-azidooctyl 2-acetamido-2-deoxy-β-D-glucopyranoside 、 苯甲醛二甲缩醛 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以84%的产率得到8-azidooctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the ‘primer–adaptor’ trisaccharide moiety of Escherichia coli O8, O9, and O9a lipopolysaccharide

  摘要：

  Described is the synthesis of the trisaccharide alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->3)-beta-D-GlcpNAcO(CH2)(8)N-3, the glycan portion of which corresponds to the 'adaptor-primer' moiety linking the O-chain and core oligosaccharide in the lipopolysaccharide of several Escherichia coli and Klebsiella pneumoniae serotypes. This report represents the first synthesis of this trisaccharide motif, and in the route involved, a key step is a [2+1] coupling of a protected Manp-(1-->3)-alpha-D-Manp glycosyl donor with a GlcpNAc acceptor. The azido group was included in the target to facilitate future preparation of neoglycoconjugates. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.08.020