methyl (3-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-altropyranosyl)-(1->3)-4-azido-2,4,6-trideoxy-2-trichloroacetamido-β-D-galactopyranoside | 280569-73-5

• 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)-(1->3)-4-azido-2,4,6-trideoxy-2-trichloroacetamido-β-D-galactopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-5-azido-4-[(2S,3S,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-4-phenylmethoxy-3-[(2,2,2-trichloroacetyl)amino]oxan-2-yl]oxy-2-methoxy-6-methyloxan-3-yl]-2,2,2-trichloroacetamide
• CAS: 280569-73-5
• 化学式: C₂₄H₂₉Cl₆N₅O₉
• 分子量: 744.24
• InChiKey: CUFKBGZZTNIOER-BYBKGMCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (3-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-altropyranosyl)-(1->3)-4-azido-2,4,6-trideoxy-2-trichloroacetamido-β-D-galactopyranoside 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 以70%的产率得到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
• 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 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 、 乙酸乙酯 、 乙腈 为溶剂， 反应 27.25h， 生成 methyl (3-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-altropyranosyl)-(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