(glycolyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-manno-2-nonulopyranosid)spirocyclic lactone | 195251-43-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (glycolyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-manno-2-nonulopyranosid)spirocyclic lactone
• 英文别名: [(2R,3S)-3-[(6R,8R,9R,10S)-9-acetamido-10-acetyloxy-5-oxo-1,4,7-trioxaspiro[5.5]undecan-8-yl]-2,3-diacetyloxypropyl] acetate
• CAS: 195251-43-5
• 化学式: C₂₁H₂₉NO₁₃
• 分子量: 503.46
• InChiKey: IPTYAPCCHFDTNB-YKFXCJJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (glycolyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-manno-2-nonulopyranosid)spirocyclic lactone 在 sodium hydroxide 、 Dowex-50 H⁺ resin 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 吡啶 为溶剂， 反应 79.0h， 生成 glycinyl-(glycolyl-5-acetamido-3,5-dideoxy-β-D-manno-2-nonulopyranosid)amide
  参考文献：
  名称：

  Ring opening of sialyllactones with glycine esters: Synthesis of selectively protected glycinyl-NeuAc saccharopeptides

  摘要：

  Two different classes of sialyllactones were prepared as potential substrates for ring opening reactions with naturally occurring amino acids. The sialyllactones underwent reaction with glycine ethyl ester hydrochloride salt to afford selectively protected glycine-NeuAc adducts. The reactions could be performed on NeuAc derivatives capable of serving as glycosylation donors. These compounds represent a new class of saccharopeptides, composed of sugar amino acids and naturally occurring amino acids. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00364-5
• 作为产物：
  描述：

  benzyl (2-O-glycolyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-O-manno-2-nonulopyranosid)onate 生成 (glycolyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-manno-2-nonulopyranosid)spirocyclic lactone
  参考文献：
  名称：

  Ring opening of sialyllactones with glycine esters: Synthesis of selectively protected glycinyl-NeuAc saccharopeptides

  摘要：

  Two different classes of sialyllactones were prepared as potential substrates for ring opening reactions with naturally occurring amino acids. The sialyllactones underwent reaction with glycine ethyl ester hydrochloride salt to afford selectively protected glycine-NeuAc adducts. The reactions could be performed on NeuAc derivatives capable of serving as glycosylation donors. These compounds represent a new class of saccharopeptides, composed of sugar amino acids and naturally occurring amino acids. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00364-5