| 1319717-52-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 1319717-52-6
• 化学式: C₇₃H₉₂N₁₆O₂₀Si
• 分子量: 1541.71
• InChiKey: ZVSAQNFCYIGFRU-UZBBZNRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.94
• 重原子数：
  110.0
• 可旋转键数：
  37.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  477.16
• 氢给体数：
  2.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  N-(benzyl)benzyloxycarbonyl-5-aminopentyl 3-O-(methyl 4-O-[6-O-{methyl 2,3-diazido-4-O-tert-butyldimethylsilyl-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-4,6-O-di-tert-butylsilylidene-2-deoxy-α-D-glucopyranoside 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以96%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