N-(benzyl)benzyloxycarbonyl-5-aminopentyl 3-O-(methyl 4-O-[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 | 1319717-48-0

• 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-[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
• 英文别名: methyl (2S,3S,4R,5S,6R)-6-[[(4aR,6S,7R,8R,8aS)-7-azido-6-[5-[benzyl(phenylmethoxycarbonyl)amino]pentoxy]-2,2-ditert-butyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-4,5-diazido-3-[(2S,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyoxane-2-carboxylate
• CAS: 1319717-48-0
• 化学式: C₆₈H₈₆N₁₀O₁₆Si
• 分子量: 1327.57
• InChiKey: NGSFWSPYQNLXKK-ADGPYPDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.37
• 重原子数：
  95
• 可旋转键数：
  33
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  221
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  methyl (phenyl 2,3-diazido-4-O-tert-butyldimethylsilyl-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate) 、 N-(benzyl)benzyloxycarbonyl-5-aminopentyl 3-O-(methyl 4-O-[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 三叔丁基膦 、 二苯基亚砜 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.83h， 以74%的产率得到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
  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 O-(methyl 4-O-[2,3,4-tri-O-benzyl-6-O-{9-fluorenylmethoxycarbonyl}-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 吡啶 、 三乙胺 作用下， 反应 3.0h， 以94%的产率得到N-(benzyl)benzyloxycarbonyl-5-aminopentyl 3-O-(methyl 4-O-[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
  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