O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-(2->8)-methyl (allyl 4,5-O-carbonyl-7-O-chloroacetyl-3-deoxy-β-D-manno-2-octulopyranosid)onate | 153580-12-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-(2->8)-methyl (allyl 4,5-O-carbonyl-7-O-chloroacetyl-3-deoxy-β-D-manno-2-octulopyranosid)onate
• CAS: 153580-12-2
• 化学式: C₃₂H₄₁ClO₂₁
• 分子量: 797.118
• InChiKey: NIKFIOGAGIGOHV-HOZSGQGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  54.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  256.55
• 氢给体数：
  0.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-(2->8)-methyl (allyl 4,5-O-carbonyl-7-O-chloroacetyl-3-deoxy-β-D-manno-2-octulopyranosid)onate 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 O-(sodium 3-deoxy-α-D-manno-2-octulopyranosylonate)-(2->8)-sodium (allyl 3-deoxy-β-D-manno-2-octulopyranosid)onate
  参考文献：
  名称：

  Synthesis and NMR spectroscopic investigation of oligosaccharides containing Kdo and l-glycero-d-manno-heptopyranosyl residues

  摘要：

  The disaccharides O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2 --> 8)-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (8), O-L-glycero-alpha-D-Manno-heptopyranosyl-(l --> 7)-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (12), and 0-alpha-D-mannopyranosyl-(1 --> 7)-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (21) and the branched trisaccharides O-L-glycero-alpha-D-manno-heptopyranosyl-(l --> 7)-[O-(sodium 3-deoXy-alpha- and -beta-D-manno-2-octulopyranosylonate)-(2 --> 8)]-sodium (allyl 3-deoXY-beta-D-manno-2-octulopyranosid)onate (15 and 16) and 0-alpha-D-mannopyranosyl-(1 --> 7)-[O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2 --> 8)]-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (24) were prepared. Per-O-acetylated mannopyranosyl or Kdo bromide derivatives were employed for the glycosylation steps under Helferich conditions, whereas the imidate derivative 9 was used for the coupling of the L-glycero-D-manno-heptopyranosyl residues. The oligosaccharides were fully characterized by NMR spectroscopic data. Their structures correspond to an artificial linkage pattern providing a potential cross-reactive epitope for antibodies directed against the inner-core-region of enterobacterial as well as chlamydial lipopolysaccharides.

  DOI：

  10.1016/0008-6215(93)87033-o
• 作为产物：
  描述：

  Methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosyl bromide)-onate 、 methyl (allyl 4,5-O-carbonyl-7-O-chloroacetyl-3-deoxy-β-D-manno-2-octulopyranosid)onate 在 4 A molecular sieve 、 氰化汞 作用下， 以 乙腈 为溶剂， 以22%的产率得到O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-(2->8)-methyl (allyl 4,5-O-carbonyl-7-O-chloroacetyl-3-deoxy-β-D-manno-2-octulopyranosid)onate
  参考文献：
  名称：

  Synthesis and NMR spectroscopic investigation of oligosaccharides containing Kdo and l-glycero-d-manno-heptopyranosyl residues

  摘要：

  The disaccharides O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2 --> 8)-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (8), O-L-glycero-alpha-D-Manno-heptopyranosyl-(l --> 7)-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (12), and 0-alpha-D-mannopyranosyl-(1 --> 7)-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (21) and the branched trisaccharides O-L-glycero-alpha-D-manno-heptopyranosyl-(l --> 7)-[O-(sodium 3-deoXy-alpha- and -beta-D-manno-2-octulopyranosylonate)-(2 --> 8)]-sodium (allyl 3-deoXY-beta-D-manno-2-octulopyranosid)onate (15 and 16) and 0-alpha-D-mannopyranosyl-(1 --> 7)-[O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2 --> 8)]-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (24) were prepared. Per-O-acetylated mannopyranosyl or Kdo bromide derivatives were employed for the glycosylation steps under Helferich conditions, whereas the imidate derivative 9 was used for the coupling of the L-glycero-D-manno-heptopyranosyl residues. The oligosaccharides were fully characterized by NMR spectroscopic data. Their structures correspond to an artificial linkage pattern providing a potential cross-reactive epitope for antibodies directed against the inner-core-region of enterobacterial as well as chlamydial lipopolysaccharides.

  DOI：

  10.1016/0008-6215(93)87033-o