(2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate | 213185-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[ClAc(-3)][Bn(-4)]Rha(a1-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-3)GlcNAc4Ac6Ac(a1-3)[Bz(-2)][Bn(-4)]Rha(a)-O-C(NH)CCl3；[(2S,3R,4R,5S,6S)-4-[(2R,3R,4R,5S,6R)-3-acetamido-5-acetyloxy-6-(acetyloxymethyl)-4-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R,5S,6S)-3-benzoyloxy-4-(2-chloroacetyl)oxy-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyl-5-phenylmethoxy-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 213185-43-4
• 化学式: C₈₃H₈₈Cl₄N₂O₂₄
• 分子量: 1639.42
• InChiKey: ADUVLJKKQJNHFE-YXIIVRTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  113
• 可旋转键数：
  39
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  304
• 氢给体数：
  2
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  6-羟基己酸甲酯 、 (2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以73%的产率得到5-methoxycarbonylpentyl (2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of Glycoconjugate Vaccines against Shigella dysenteriae Type 1

  摘要：

  Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglyconlinked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.

  DOI：

  10.1021/jo980660a
• 作为产物：
  描述：

  三氯乙腈 、 (2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-L-rhamnopyranose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以69%的产率得到(2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of Glycoconjugate Vaccines against Shigella dysenteriae Type 1

  摘要：

  Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglyconlinked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.

  DOI：

  10.1021/jo980660a