methyl (3-O-acetyl-4-azido-2,4,6-trideoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 3-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-altropyranosid)uronate | 280569-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3-O-acetyl-4-azido-2,4,6-trideoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 3-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-altropyranosid)uronate
• 英文别名: methyl (2S,3S,4S,5S,6S)-3-[(2S,3R,4R,5S,6R)-4-acetyloxy-5-azido-6-methyl-3-[(2,2,2-trichloroacetyl)amino]oxan-2-yl]oxy-6-methoxy-4-phenylmethoxy-5-[(2,2,2-trichloroacetyl)amino]oxane-2-carboxylate
• CAS: 280569-66-6
• 化学式: C₂₇H₃₁Cl₆N₅O₁₁
• 分子量: 814.288
• InChiKey: IWRAVMODOCSTQA-XJEVUXGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  171
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl (3-O-acetyl-4-azido-2,4,6-trideoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 3-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-altropyranosid)uronate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 (2S,3S,4S,5S,6S)-5-Amino-3-((2S,3R,4R,5R,6R)-3-amino-5-azido-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthetic Studies Towards theO-Specific Polysaccharide ofShigella Sonnei

  摘要：

  Synthetic routes are described to zwitter-ionic disaccharides that are diastereoisomerically related to frame-shifted repeating units of the title polysaccharide that contains 2-acetamido-4-amino-2,4,6-trideoxy-D-galactose and 2-acetamido-2-deoxy-L-altruronic acid. The intermediates corresponding to the trideoxygalactose residue feature acylamino functions at C-2 and an azido group at C-4. Best results were obtained with N-phthaloyl- and N-trichloroacetyl-protected derivatives. The intermediates corresponding to the uronic acid residue were either a D-altruronic acid-derived acceptor or a D-altrose-derived donor in which C-6 was oxidized after disaccharide formation.

  DOI：

  10.1080/07328300008544079
• 作为产物：
  描述：

  methyl 2-azido-3-O-benzyl-2-deoxy-α-D-altropyranoside 在 palladium on activated charcoal 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 氢气 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.33h， 生成 methyl (3-O-acetyl-4-azido-2,4,6-trideoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 3-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-altropyranosid)uronate
  参考文献：
  名称：

  Synthetic Studies Towards theO-Specific Polysaccharide ofShigella Sonnei

  摘要：

  Synthetic routes are described to zwitter-ionic disaccharides that are diastereoisomerically related to frame-shifted repeating units of the title polysaccharide that contains 2-acetamido-4-amino-2,4,6-trideoxy-D-galactose and 2-acetamido-2-deoxy-L-altruronic acid. The intermediates corresponding to the trideoxygalactose residue feature acylamino functions at C-2 and an azido group at C-4. Best results were obtained with N-phthaloyl- and N-trichloroacetyl-protected derivatives. The intermediates corresponding to the uronic acid residue were either a D-altruronic acid-derived acceptor or a D-altrose-derived donor in which C-6 was oxidized after disaccharide formation.

  DOI：

  10.1080/07328300008544079