4-O-acetyl-2,3-di-O-benzoyl-6-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate | 1448540-27-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 4-O-acetyl-2,3-di-O-benzoyl-6-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][levulinoyl(-6)]Glc4Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-3-acetyloxy-5-benzoyloxy-2-(4-oxopentanoyloxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl] benzoate
• CAS: 1448540-27-9
• 化学式: C₂₉H₂₈Cl₃NO₁₁
• 分子量: 672.9
• InChiKey: HMUXNJIZGICFEF-UFOFBUIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  165
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-O-acetyl-2,3-di-O-benzoyl-6-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate 、 p-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以82%的产率得到p-methoxyphenyl 4-O-acetyl-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranosyl-(1→3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Immunological Characterization of Modified Hyaluronic Acid Hexasaccharide Conjugates

  摘要：

  The synthesis of a tetanus toxoid (TT)-conjugate of a hyaluronic acid (HA) hexasaccharide is described. The compound was intended for use in monitoring HA levels as a disease marker and as a potential vaccine against Group A Streptococcus (GAS) infections. We also report the synthesis of a chemically modified HA-hexasaccharide-TT conjugate in which the N-acetyl moiety of the N-acetyl-D-glucosamine residue is replaced with an N-propionyl unit in order to enhance immunogenicity. The oligosaccharides are synthesized in a convergent manner. The TT-conjugate syntheses rely on the reaction of the amines on the 6-aminohexyl aglycon of the hexasaccharides with diethyl squarate to give the monoethyl squarate adducts. Subsequent reactions with lysine epsilon-amino groups on TT then give the glycoconjugates containing an average of 8 hexasaccharide haptens per TT molecule. Immunological studies in mice show very similar antibody responses with both conjugates, suggesting that the N-acetyl groups of the glucosaminyl residues of the HA-hexasaccharide are not a critical part of the epitope recognized by the anti-HA polyclonal immune response. Furthermore, it would appear that the N-acyl moieties are not in close contact with the amino acid residues of the antibody combining sites.

  DOI：

  10.1021/jo4012442
• 作为产物：
  描述：

  4-methoxyphenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 在 吡啶 、 ammonium cerium (IV) nitrate 、 2-氯-1-甲基吡啶碘化物 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 氯仿 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 3.33h， 生成 4-O-acetyl-2,3-di-O-benzoyl-6-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis and Immunological Characterization of Modified Hyaluronic Acid Hexasaccharide Conjugates

  摘要：

  The synthesis of a tetanus toxoid (TT)-conjugate of a hyaluronic acid (HA) hexasaccharide is described. The compound was intended for use in monitoring HA levels as a disease marker and as a potential vaccine against Group A Streptococcus (GAS) infections. We also report the synthesis of a chemically modified HA-hexasaccharide-TT conjugate in which the N-acetyl moiety of the N-acetyl-D-glucosamine residue is replaced with an N-propionyl unit in order to enhance immunogenicity. The oligosaccharides are synthesized in a convergent manner. The TT-conjugate syntheses rely on the reaction of the amines on the 6-aminohexyl aglycon of the hexasaccharides with diethyl squarate to give the monoethyl squarate adducts. Subsequent reactions with lysine epsilon-amino groups on TT then give the glycoconjugates containing an average of 8 hexasaccharide haptens per TT molecule. Immunological studies in mice show very similar antibody responses with both conjugates, suggesting that the N-acetyl groups of the glucosaminyl residues of the HA-hexasaccharide are not a critical part of the epitope recognized by the anti-HA polyclonal immune response. Furthermore, it would appear that the N-acyl moieties are not in close contact with the amino acid residues of the antibody combining sites.

  DOI：

  10.1021/jo4012442