(2R,3S,4R,5R,6R)-3-((1H-imidazole-1-carbonothioyl)oxy)-2-((benzoyloxy)methyl)-5-(1,3-dioxoisoindolin-2-yl)-6-methoxytetrahydro-2H-pyran-4-yl benzoate | 157553-82-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-3-((1H-imidazole-1-carbonothioyl)oxy)-2-((benzoyloxy)methyl)-5-(1,3-dioxoisoindolin-2-yl)-6-methoxytetrahydro-2H-pyran-4-yl benzoate
• CAS: 157553-82-7
• 化学式: C₃₃H₂₇N₃O₉S
• 分子量: 641.658
• InChiKey: LJPHQIBCGASXMQ-UYPZCZSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  135.49
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-3-((1H-imidazole-1-carbonothioyl)oxy)-2-((benzoyloxy)methyl)-5-(1,3-dioxoisoindolin-2-yl)-6-methoxytetrahydro-2H-pyran-4-yl benzoate 在 偶氮二异丁腈 、 硫酸 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 1-O-acetyl-3,6-di-O-benzoyl-2,4-dideoxy-2-phthalimido-α-D-xylo-hexopyranose
  参考文献：
  名称：

  Synthesis of the 2''-Hydroxy, 4''-Deoxy and 4''-Epi Analogues of beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal, the Terminal Trisaccharide of Globotetraose.

  摘要：

  Radical deoxygenation of methyl 3,6-di-O-benzoyl-2-deoxy-4-0-imidazol-1-yl-thiocarbonyloxy-2-phthalimido-beta-D-glucopyranoside 5 gave methyl 3,6-di-O-benzoyl-2,4-dideoxy-2-phthalimido-beta-D-glucopyranoside 6, which was converted into the corresponding methyl thioglycoside donor 9. Methylsulfenyl trifluoromethane-sulfonate-promoted glycosylation of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-D-galactopyranosyl)-beta-D-galactopyranoside 10, followed by removal of protecting groups gave the 4''-deoxy analogue 12 of the terminal trisaccharide of globotetraose. Silver trifluoromethanesulfonate-promoted glycosylation of the same disaccharide alcohol 10 with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-alpha/beta-D-glucopyranosyl bromide 13 and 2.3,4,6-tetra-0-acetyl-alpha-D-galactopyranosyl bromide 16, followed by deblocking, gave the 2''-hydroxy and 4''-epi analogues 15 and 18. respectively.

  DOI：

  10.3891/acta.chem.scand.48-0356
• 作为产物：
  描述：

  甲基 2-脱氧-2-N-苯二甲酰亚氨基-beta-D-吡喃葡萄糖苷 在 吡啶 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 生成 (2R,3S,4R,5R,6R)-3-((1H-imidazole-1-carbonothioyl)oxy)-2-((benzoyloxy)methyl)-5-(1,3-dioxoisoindolin-2-yl)-6-methoxytetrahydro-2H-pyran-4-yl benzoate
  参考文献：
  名称：

  Synthesis of the 2''-Hydroxy, 4''-Deoxy and 4''-Epi Analogues of beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal, the Terminal Trisaccharide of Globotetraose.

  摘要：

  Radical deoxygenation of methyl 3,6-di-O-benzoyl-2-deoxy-4-0-imidazol-1-yl-thiocarbonyloxy-2-phthalimido-beta-D-glucopyranoside 5 gave methyl 3,6-di-O-benzoyl-2,4-dideoxy-2-phthalimido-beta-D-glucopyranoside 6, which was converted into the corresponding methyl thioglycoside donor 9. Methylsulfenyl trifluoromethane-sulfonate-promoted glycosylation of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-D-galactopyranosyl)-beta-D-galactopyranoside 10, followed by removal of protecting groups gave the 4''-deoxy analogue 12 of the terminal trisaccharide of globotetraose. Silver trifluoromethanesulfonate-promoted glycosylation of the same disaccharide alcohol 10 with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-alpha/beta-D-glucopyranosyl bromide 13 and 2.3,4,6-tetra-0-acetyl-alpha-D-galactopyranosyl bromide 16, followed by deblocking, gave the 2''-hydroxy and 4''-epi analogues 15 and 18. respectively.

  DOI：

  10.3891/acta.chem.scand.48-0356