| 1319717-54-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1319717-54-8
• 化学式: C₆₅H₇₄N₁₆O₂₀
• 分子量: 1399.4
• InChiKey: XBPLLIFGCMJMDP-DIZBCWKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.73
• 重原子数：
  101.0
• 可旋转键数：
  35.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  510.16
• 氢给体数：
  5.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 生成
  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：

  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