phenyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1->3)-(4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside | 213185-38-7

• 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-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1->3)-(4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside
• 英文别名: [(2S,3R,4R,5S,6S)-4-[(2R,3R,4R,5S,6R)-5-acetyloxy-6-(acetyloxymethyl)-3-azido-4-[(2S,3R,4S,5S,6R)-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyl-5-phenylmethoxy-2-phenylsulfanyloxan-3-yl] benzoate
• CAS: 213185-38-7
• 化学式: C₇₁H₇₅N₃O₁₇S
• 分子量: 1274.45
• InChiKey: JHESCVPNCINHHU-KSRJMARGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.6
• 重原子数：
  92
• 可旋转键数：
  32
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  220
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  phenyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1->3)-(4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside 在 三苯基膦 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以7.9 g的产率得到phenyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1->3)-(4,6-di-O-acetyl-2-amino-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 3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 氯 、 sodium hydride 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 生成 phenyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1->3)-(4,6-di-O-acetyl-2-azido-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

文献信息

• SyntheticShigella Vaccines: A Carbohydrate–Protein Conjugate with Totally Synthetic Hexadecasaccharide Haptens
  作者：Vince Pozsgay

  DOI：10.1002/(sici)1521-3773(19980202)37:1/2<138::aid-anie138>3.0.co;2-t

  日期：1998.2.2