methyl [(3-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-altropyranosyl)uronic acid]-(1->3)-4-azido-2,4,6-trideoxy-2-trichloroacetamido-β-D-galactopyranoside | 280569-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [(3-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-altropyranosyl)uronic acid]-(1->3)-4-azido-2,4,6-trideoxy-2-trichloroacetamido-β-D-galactopyranoside
• 英文别名: (2S,3S,4S,5S,6S)-6-[(2R,3R,4R,5S,6R)-5-azido-2-methoxy-6-methyl-3-[(2,2,2-trichloroacetyl)amino]oxan-4-yl]oxy-3-hydroxy-4-phenylmethoxy-5-[(2,2,2-trichloroacetyl)amino]oxane-2-carboxylic acid
• CAS: 280569-74-6
• 化学式: C₂₄H₂₇Cl₆N₅O₁₀
• 分子量: 758.224
• InChiKey: JOLQWXBIHMWBSO-NULVTHBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  176
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl [(3-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-altropyranosyl)uronic acid]-(1->3)-4-azido-2,4,6-trideoxy-2-trichloroacetamido-β-D-galactopyranoside 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-6-((2R,3R,4R,5S,6R)-3-amino-5-azido-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-benzyloxy-3-hydroxy-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：

  ethyl 4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α,β-D-altropyranoside 在 platinum(IV) oxide 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 、 三乙胺 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 27.75h， 生成 methyl [(3-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-altropyranosyl)uronic acid]-(1->3)-4-azido-2,4,6-trideoxy-2-trichloroacetamido-β-D-galactopyranoside
  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