N-(benzyl)benzyloxycarbonyl-5-aminopentyl 3-O-(methyl-4-O-[6-O-{methyl 2,3-diazido-2,3-dideoxy-β-D-mannopyranosyl uronate}-2,3,4-tri-O-benzyl-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-β-D-mannopyranosyl uronate)-2-azido-2-deoxy-α-D-glucopyranoside | 1319717-51-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(benzyl)benzyloxycarbonyl-5-aminopentyl 3-O-(methyl-4-O-[6-O-{methyl 2,3-diazido-2,3-dideoxy-β-D-mannopyranosyl uronate}-2,3,4-tri-O-benzyl-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-β-D-mannopyranosyl uronate)-2-azido-2-deoxy-α-D-glucopyranoside
• 英文别名: methyl (2S,3S,4R,5S,6R)-4,5-diazido-6-[[(2R,3R,4S,5R,6S)-6-[(2S,3S,4R,5S,6R)-4,5-diazido-6-[(2S,3R,4R,5S,6R)-3-azido-2-[5-[benzyl(phenylmethoxycarbonyl)amino]pentoxy]-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-methoxycarbonyloxan-3-yl]oxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-3-hydroxyoxane-2-carboxylate
• CAS: 1319717-51-5
• 化学式: C₆₇H₇₈N₁₆O₂₀
• 分子量: 1427.45
• InChiKey: GDOKQHVFSSRJNW-DRBCNSPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  103
• 可旋转键数：
  38
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  316
• 氢给体数：
  3
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  N-(benzyl)benzyloxycarbonyl-5-aminopentyl 3-O-(methyl-4-O-[6-O-{methyl 2,3-diazido-2,3-dideoxy-β-D-mannopyranosyl uronate}-2,3,4-tri-O-benzyl-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-β-D-mannopyranosyl uronate)-2-azido-2-deoxy-α-D-glucopyranoside 在 双氧水 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以83 mg的产率得到
  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
• 作为产物：
  描述：

  在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以75%的产率得到N-(benzyl)benzyloxycarbonyl-5-aminopentyl 3-O-(methyl-4-O-[6-O-{methyl 2,3-diazido-2,3-dideoxy-β-D-mannopyranosyl uronate}-2,3,4-tri-O-benzyl-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-β-D-mannopyranosyl uronate)-2-azido-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