methyl 3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-trichloroacetamido-α-D-altropyranoside | 280569-54-2

• 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-6-O-chloroacetyl-2-deoxy-2-trichloroacetamido-α-D-altropyranoside
• 英文别名: [(2R,3S,4S,5S,6S)-3-hydroxy-6-methoxy-4-phenylmethoxy-5-[(2,2,2-trichloroacetyl)amino]oxan-2-yl]methyl 2-chloroacetate
• CAS: 280569-54-2
• 化学式: C₁₈H₂₁Cl₄NO₇
• 分子量: 505.179
• InChiKey: FQCISCPJJBDZMB-GAUGTXIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 3-O-acetyl-4-azido-2,4,6-trideoxy-1-thio-2-trichloroacetamido-β-D-galactopyranoside 、 methyl 3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-trichloroacetamido-α-D-altropyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.33h， 以24%的产率得到methyl (3-O-acetyl-4-azido-2,4,6-trideoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-trichloroacetamido-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：

  methyl 2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranoside 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl 3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-trichloroacetamido-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.