methyl (4-azido-2-acetamido-2,4,6-trideoxy-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3-O-benzyl-2-deoxy-α-D-altropyranosid)uronic acid | 280569-67-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (4-azido-2-acetamido-2,4,6-trideoxy-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3-O-benzyl-2-deoxy-α-D-altropyranosid)uronic acid
• 英文别名: (2S,3S,4S,5S,6S)-5-acetamido-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-azido-4-hydroxy-6-methyloxan-2-yl]oxy-6-methoxy-4-phenylmethoxyoxane-2-carboxylic acid
• CAS: 280569-67-7
• 化学式: C₂₄H₃₃N₅O₁₀
• 分子量: 551.554
• InChiKey: JOLNYXRVMGVZOU-LKSRPSCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  39
• 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 (4-azido-2-acetamido-2,4,6-trideoxy-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3-O-benzyl-2-deoxy-α-D-altropyranosid)uronic acid 在 palladium dihydroxide 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以78%的产率得到methyl (2-acetamido-4-amino-2,4,6-trideoxy-β-D-galactopyranosyl)-(1->4)-(2-acetamido-2-deoxy-α-D-altropyranosid)uronic 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：

  3-O-acetyl-4-azido-2,4,6-trideoxy-2-phthalimido-1-thio-β-D-galactopyranoside 在 吡啶 、 sodium hydroxide 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 乙二胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 78.66h， 生成 methyl (4-azido-2-acetamido-2,4,6-trideoxy-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3-O-benzyl-2-deoxy-α-D-altropyranosid)uronic 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

文献信息

• Synthetic Studies Towards the<i>O</i>-Specific Polysaccharide of<i>Shigella Sonnei</i>
  作者：Adél Medgyes、István Bajza、Erzsébet Farkas、Vince Pozsgay、András Lipták

  DOI：10.1080/07328300008544079

  日期：2000.1

  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.