methyl-5-acetamido-7,8,9-tri-O-benzoyl-3,5-dideoxy-β-D-manno-2-nonulopyranoside-1,4 lactone | 195251-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-5-acetamido-7,8,9-tri-O-benzoyl-3,5-dideoxy-β-D-manno-2-nonulopyranoside-1,4 lactone
• 英文别名: I(2)-Neuraminic acid, N-acetyl-2-O-methyl-, I(3)-lactone, 7,8,9-tribenzoate；[(2R,3S)-3-[(1S,3R,4R,5S)-4-acetamido-1-methoxy-7-oxo-2,6-dioxabicyclo[3.2.1]octan-3-yl]-2,3-dibenzoyloxypropyl] benzoate
• CAS: 195251-36-6
• 化学式: C₃₃H₃₁NO₁₁
• 分子量: 617.609
• InChiKey: DEZYCIUWODKLSC-RIBVAUNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl-5-acetamido-7,8,9-tri-O-benzoyl-3,5-dideoxy-β-D-manno-2-nonulopyranoside-1,4 lactone 在 4-二甲氨基吡啶 、 Amberlite IRA 400 (OH^-) ion exchange resin 作用下， 以 甲醇 、 氘代二甲亚砜 为溶剂， 反应 220.0h， 生成 glycinyl-(methyl-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：

  N-acetyl neuraminic acid 在 吡啶 、 sodium hydroxide 、 Dowex H(+) 作用下， 以 水 为溶剂， 反应 18.0h， 生成 methyl-5-acetamido-7,8,9-tri-O-benzoyl-3,5-dideoxy-β-D-manno-2-nonulopyranoside-1,4 lactone
  参考文献：
  名称：

  Synthesis of 13C enriched sialyllactones and their characterization using isotope edited inverse detected NMR spectroscopy

  摘要：

  C-13 enriched monosaccharide based sialyllactones were prepared in order to perform isotope edited NMR experiments for their characterization. In the inverse detected experiments only those protons long range coupled to the enriched nuclei are detected, providing a potentially powerful tool for studying in vitro sialyllactone formation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00237-2