phenyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-1-thio-α-L-rhamnopyranoside | 213185-32-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-1-thio-α-L-rhamnopyranoside
• 英文别名: Bz(-2)[ClAc(-3)][Bn(-4)]Rha(a)-SPh；[(2S,3R,4R,5S,6S)-4-(2-chloroacetyl)oxy-6-methyl-5-phenylmethoxy-2-phenylsulfanyloxan-3-yl] benzoate
• CAS: 213185-32-1
• 化学式: C₂₈H₂₇ClO₆S
• 分子量: 527.038
• InChiKey: MCTUPHCCUHMUBR-IVMKFSNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-1-thio-α-L-rhamnopyranoside 在 mercury(II) trifluoroacetate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以87%的产率得到2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α,β-L-rhamnopyranose
  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 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 在 吡啶 、 D(+)-10-樟脑磺酸 、 sodium hydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.42h， 生成 phenyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-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

文献信息

• Synthesis of Glycoconjugate Vaccines against <i>Shigella dysenteriae</i> Type 1
  作者：Vince Pozsgay

  DOI：10.1021/jo980660a

  日期：1998.8.1

  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.