5-aminopentyl 3-O-(4-O-[6-O-{2,3-di-N-acetamido-2,3-dideoxy-β-D-mannopyranosyl uronate}-α-D-glucopyranosyl]-2,3-di-N-acetamido-2,3-dideoxy-β-D-mannopyranosyl uronate)-2-N-acetamido-2-deoxy-α-D-glucopyranoside | 1319717-53-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-aminopentyl 3-O-(4-O-[6-O-{2,3-di-N-acetamido-2,3-dideoxy-β-D-mannopyranosyl uronate}-α-D-glucopyranosyl]-2,3-di-N-acetamido-2,3-dideoxy-β-D-mannopyranosyl uronate)-2-N-acetamido-2-deoxy-α-D-glucopyranoside
• 英文别名: (2S,3S,4R,5S,6R)-4,5-diacetamido-6-[[(2R,3S,4S,5R,6S)-6-[(2S,3S,4R,5S,6R)-4,5-diacetamido-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-(5-aminopentoxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-hydroxyoxane-2-carboxylic acid
• CAS: 1319717-53-7
• 化学式: C₃₉H₆₄N₆O₂₃
• 分子量: 984.964
• InChiKey: LFZUKBDPLGHIAB-FXRBOMGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.6
• 重原子数：
  68
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  441
• 氢给体数：
  14
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 以12 mg的产率得到5-aminopentyl 3-O-(4-O-[6-O-{2,3-di-N-acetamido-2,3-dideoxy-β-D-mannopyranosyl uronate}-α-D-glucopyranosyl]-2,3-di-N-acetamido-2,3-dideoxy-β-D-mannopyranosyl uronate)-2-N-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of 2,3-Diamino-2,3-dideoxy-β-d-mannopyranosyl Uronates

  摘要：

  With the aim to find an efficient synthetic procedure for the construction of 2,3-diamino-2,3-dideoxy-beta-D-mannuronic acids, we evaluated three mannosyl donors: (S)-phenyl 4,6-di-O-acetyl-2,3-diazido mannopyranoside, (S)-phenyl 2,3-diazido-4,6-O-benzylidene mannopyranoside, and (S)-phenyl 2,3-diazido mannopyranosyl methyl uronate. The first two mannosylating agents are rather unselective or slightly a-selective in their condensation with three different acceptors. The mannuronic acid donor on the other hand reliably provides the desired beta-mannosidic linkage. A mechanistic rationale is put forward to account for the different behavior of the three donor types. Suitably protected 2,3-diazido mannuronic acids were employed to construct the all-cis-linked tetrasaccharide repeating unit of the capsular polysaccharide of Bacillus stearothermophilus, featuring two 2,3-diacetamido-2,3-dideoxy-beta-D-mannuronic acids.

  DOI：

  10.1021/jo201179p