8-(N-2-aminoethyl)carboxamidooctyl 4-O-(2-acetamido-2-deoxy-β-Dgalactopyranosyl)-β-D-galactopyranoside | 236743-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-(N-2-aminoethyl)carboxamidooctyl 4-O-(2-acetamido-2-deoxy-β-Dgalactopyranosyl)-β-D-galactopyranoside
• CAS: 236743-50-3
• 化学式: C₂₅H₄₇N₃O₁₂
• 分子量: 581.661
• InChiKey: RVXYQAXBRBQPBF-ABPMYTFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.42
• 重原子数：
  40.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  242.52
• 氢给体数：
  9.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  己二酸 、 8-(N-2-aminoethyl)carboxamidooctyl 4-O-(2-acetamido-2-deoxy-β-Dgalactopyranosyl)-β-D-galactopyranoside 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以81%的产率得到N,N'-di-{8-[4-O-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-β-D-galactopyranosyloxy]octylcarbonylaminoethyl}adipamide
  参考文献：
  名称：

  Synthesis of Simple Multivalent β-D-GalNAc-(1→4)-β-D-Gal Oligomers as Probes for Investigating the Interactions ofP. AeruginosaPili with Multivalent Receptors

  摘要：

  Five multivalent beta-D-GalNAc-(1-->4)-beta-D-Gal oligomers were selected and synthesized as probes for investigating the adhesin-receptor interactions of P. aeruginosa pill with multivalent receptors. They were synthesized by the amide coupling reactions of 8-(N-2-aminoethyl)carboxamidooctyl 4-O-(2-acetamido-2-deoxy-beta-D-galactopyranosyl)beta-D-galactopyranoside (7) with EDTA dianhydride, EDTA, Kemp's triacid and adipic acid with EDC, DIC and DCC combined with HOBt as coupling reagents and by the reaction of per-O-acetylated 7 with 1,3,5-benzenetricarbonyl trichloride followed by de-O-acetylation. These resulting multivalent compounds contain flexible C-9 spacer arms as linkers attached to either flexible hydrophilic moieties or rigid hydrophobic cores.

  DOI：

  10.1080/07328309908544014
• 作为产物：
  描述：

  8-(methoxycarbonyl)octyl β-D-galactopyranoside 在 2,3,5-三甲基吡啶 、 盐酸 、 silver trifluoromethanesulfonate 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 8-(N-2-aminoethyl)carboxamidooctyl 4-O-(2-acetamido-2-deoxy-β-Dgalactopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Simple Multivalent β-D-GalNAc-(1→4)-β-D-Gal Oligomers as Probes for Investigating the Interactions ofP. AeruginosaPili with Multivalent Receptors

  摘要：

  Five multivalent beta-D-GalNAc-(1-->4)-beta-D-Gal oligomers were selected and synthesized as probes for investigating the adhesin-receptor interactions of P. aeruginosa pill with multivalent receptors. They were synthesized by the amide coupling reactions of 8-(N-2-aminoethyl)carboxamidooctyl 4-O-(2-acetamido-2-deoxy-beta-D-galactopyranosyl)beta-D-galactopyranoside (7) with EDTA dianhydride, EDTA, Kemp's triacid and adipic acid with EDC, DIC and DCC combined with HOBt as coupling reagents and by the reaction of per-O-acetylated 7 with 1,3,5-benzenetricarbonyl trichloride followed by de-O-acetylation. These resulting multivalent compounds contain flexible C-9 spacer arms as linkers attached to either flexible hydrophilic moieties or rigid hydrophobic cores.

  DOI：

  10.1080/07328309908544014