phenyl [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-1-thio-α-L-rhamnopyranoside | 213185-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl [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-1-thio-α-L-rhamnopyranoside
• 英文别名: Bn(-3)[Bn(-4)][Bn(-6)]Gal(a1-3)GlcNAc4Ac6Ac(a1-3)[Bz(-2)][Bn(-4)]Rha(a)-SPh；[(2S,3R,4R,5S,6S)-4-[(2R,3R,4R,5S,6R)-3-acetamido-5-acetyloxy-6-(acetyloxymethyl)-4-[(2S,3R,4R,5S,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyl-5-phenylmethoxy-2-phenylsulfanyloxan-3-yl] benzoate
• CAS: 213185-40-1
• 化学式: C₆₅H₇₁NO₁₇S
• 分子量: 1170.34
• InChiKey: SBWBHSQBRSOVAG-IKLVZPRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  84
• 可旋转键数：
  28
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  237
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl trichloroacetimidate 、 phenyl [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-1-thio-α-L-rhamnopyranoside 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到phenyl (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-1-thio-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：

  phenyl 2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 tetrafluoroboric acid 、 2,6-二叔丁基-4-甲基吡啶 、 ammonium cerium(IV) nitrate 、 4 A molecular sieve 、 D(+)-10-樟脑磺酸 、 silver trifluoromethanesulfonate 、 硫脲 、 三苯基膦 、 三氟甲烷磺酸甲酯 作用下， 以 吡啶 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 225.0h， 生成 phenyl [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-1-thio-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