n-propyl 2-amino-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-[(R)-1'-carboxyethyl]-2-deoxy-α-D-glucopyranoside | 1628714-98-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: n-propyl 2-amino-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-[(R)-1'-carboxyethyl]-2-deoxy-α-D-glucopyranoside
• 英文别名: GlcN(b1-4)MurNAc(a)-O-Pr；(2R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-3-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(hydroxymethyl)-6-propoxyoxan-4-yl]oxypropanoic acid
• CAS: 1628714-98-6
• 化学式: C₂₀H₃₆N₂O₁₂
• 分子量: 496.512
• InChiKey: HNNLNVWBZYEUCQ-QFKAEUCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  220
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  allyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranosyl-(1→4)-6-O-benzyl-3-O-benzyloxycarbonyl-2-N-trichloroethoxycarbonylamino-2-deoxy-α-D-glucopyranoside 在 10 wt% Pd(OH)2 on carbon 、 氢气 、 sodium hydride 、 溶剂黄146 、 potassium hydroxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 mineral oil 为溶剂， 反应 3.75h， 生成 n-propyl 2-amino-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-[(R)-1'-carboxyethyl]-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Partially N-Acetylated Chitooligosaccharides and Muropeptides

  摘要：

  Partially N-acetylated chitooligosaccharides and muropeptides are referred to as microbial associated molecular patterns (MAMPs). To shed light on the molecular basis of their recognition by the innate immunity system of living organisms, their production in pure form is necessary. To this end, we present here the first synthetic strategy for the obtainment of a series of partially N-acetylated muropeptides as well as of a chitodisaccharide and a chitotetrasaccharide, all possessing a well-defined N-acetylation pattern.

  DOI：

  10.1055/s-0033-1340323