2-acetamido-4-O-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranose | 1203588-94-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-4-O-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranose
• 英文别名: 2-acetamido-4-O-(2-azido-3,6-di-O-benzyl-2-deoxy-beta-d-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-beta-d-glucopyranose；N-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-azido-5-hydroxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-hydroxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 1203588-94-6
• 化学式: C₄₂H₄₈N₄O₁₀
• 分子量: 768.864
• InChiKey: BVMIYDDJWMQCIR-BKPOAMSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  56
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-acetamido-4-O-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranose 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以72%的产率得到2-amino-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Selection of protecting groups and synthesis of a β-1,4-GlcNAc-β-1,4-GlcN unit

  摘要：

  The synthesis of the disaccharide tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside, designed as a repeating unit appearing in oligo-and polysaccharides, which exhibits a distinguished "obverse-reverse" property in beta-1,4-glucan chain, was accomplished. This disaccharide was synthesized by glycosylation of a phthalimido sugar with an azido sugar. A selective removal of the two different protecting groups atC-2 for obtaining 2-acetamido-4-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-beta-D-glucopyranose indicates that the selection and combination, using phthalimido and azido as protecting groups, are an excellent strategy for synthesizing such target disaccharides.

  DOI：

  10.1007/s00706-009-0172-0
• 作为产物：
  描述：

  tert-butyldimethylsilyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 吡啶 、 甲醇 、 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 sodium methylate 、 溶剂黄146 、 乙二胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 正丁醇 为溶剂， 反应 1.0h， 生成 2-acetamido-4-O-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Selection of protecting groups and synthesis of a β-1,4-GlcNAc-β-1,4-GlcN unit

  摘要：

  The synthesis of the disaccharide tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside, designed as a repeating unit appearing in oligo-and polysaccharides, which exhibits a distinguished "obverse-reverse" property in beta-1,4-glucan chain, was accomplished. This disaccharide was synthesized by glycosylation of a phthalimido sugar with an azido sugar. A selective removal of the two different protecting groups atC-2 for obtaining 2-acetamido-4-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-beta-D-glucopyranose indicates that the selection and combination, using phthalimido and azido as protecting groups, are an excellent strategy for synthesizing such target disaccharides.

  DOI：

  10.1007/s00706-009-0172-0