phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside | 653572-82-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside
• CAS: 653572-82-8
• 化学式: C₅₂H₄₉NO₁₆S
• 分子量: 976.024
• InChiKey: XAQFHILZCIXVRR-GGFDKTNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  70.0
• 可旋转键数：
  15.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  206.75
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside 、 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以66%的产率得到
  参考文献：
  名称：

  Synthesis of a Blocked Tetrasaccharide Related to the Repeating Unit of the Antigen from Shigella dysenteriae Type 9 in the Form of Its Methyl (R)‐Pyruvate Ester and 2‐(Trimethylsilyl)Ethyl Glycoside

  摘要：

  Starting from D-mannose, D-galactose and D-glucosamine hydrochloride, two disaccharide blocks were synthesized. Schmidt's inverse addition technique of trichloroacetimidate was utilized for the construction of a disaccharide with a beta-mannosidic linkage in good yield. The other disaccharide had a methyl 4,6-(R)pyruvate ester. The two disaccharides in the appropriate form were then allowed to react in the presence of N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH) to give the desired tetrasaccharide derivative, 2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-beta-D-glucopyranosyl-(l --> 3)-2-O-benzoyl-4,6-O-[(R)-1-methoxycarbonylethylidene]-beta-D-galactopyranosyl-(I --> 4)-2,3,6-tri-O-benzyl-beta-D-mannopyranosyl-(1 --> 4)-2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-beta-D-galactopyranoside.

  DOI：

  10.1081/car-120026456
• 作为产物：
  描述：

  N-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-((4aR,6S,7R,8R,8aS)-7-hydroxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl]-acetamide 在 吡啶 、 三氟化硼乙醚 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a Blocked Tetrasaccharide Related to the Repeating Unit of the Antigen from Shigella dysenteriae Type 9 in the Form of Its Methyl (R)‐Pyruvate Ester and 2‐(Trimethylsilyl)Ethyl Glycoside

  摘要：

  Starting from D-mannose, D-galactose and D-glucosamine hydrochloride, two disaccharide blocks were synthesized. Schmidt's inverse addition technique of trichloroacetimidate was utilized for the construction of a disaccharide with a beta-mannosidic linkage in good yield. The other disaccharide had a methyl 4,6-(R)pyruvate ester. The two disaccharides in the appropriate form were then allowed to react in the presence of N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH) to give the desired tetrasaccharide derivative, 2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-beta-D-glucopyranosyl-(l --> 3)-2-O-benzoyl-4,6-O-[(R)-1-methoxycarbonylethylidene]-beta-D-galactopyranosyl-(I --> 4)-2,3,6-tri-O-benzyl-beta-D-mannopyranosyl-(1 --> 4)-2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-beta-D-galactopyranoside.

  DOI：

  10.1081/car-120026456