methyl 3-O-benzyl-2-deoxy-2-phthalimido-α-D-altropyranoside | 280569-48-4

• 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-phthalimido-α-D-altropyranoside
• 英文别名: 2-[(2S,3S,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-methoxy-4-phenylmethoxyoxan-3-yl]isoindole-1,3-dione
• CAS: 280569-48-4
• 化学式: C₂₂H₂₃NO₇
• 分子量: 413.427
• InChiKey: QJCKSASQOOXSCY-CMXRIWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  105.53
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzyl-2-deoxy-2-phthalimido-α-D-altropyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 methyl (3-O-acetyl-4-azido-2,4,6-trideoxy-2-phthalimido-β-D-galactopyranosyl)-(1->4)-3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-α-D-altropyranoside
  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：

  2-(氯羰基)苯甲酸甲酯 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 methyl 3-O-benzyl-2-deoxy-2-phthalimido-α-D-altropyranoside
  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.