methyl 4-O-(methyl 4-O-acetyl-2,3-diazido-2,3-dideoxy-β-D-mannopyranosyl uronate)-2,3,6-tri-O-benzyl-α-D-glucopyranoside | 1319717-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-(methyl 4-O-acetyl-2,3-diazido-2,3-dideoxy-β-D-mannopyranosyl uronate)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: methyl (2S,3S,4R,5S,6R)-3-acetyloxy-4,5-diazido-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxyoxane-2-carboxylate
• CAS: 1319717-36-6
• 化学式: C₃₇H₄₂N₆O₁₁
• 分子量: 746.774
• InChiKey: JEIOUUDSYMMMTE-QTUQGPIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  phenyl 4,6-di-O-acetyl-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranoside 在 吡啶 、 2,2,6,6-四甲基哌啶氧化物 、 三叔丁基膦 、 碘苯二乙酸 、 二苯基亚砜 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.33h， 生成 methyl 4-O-(methyl 4-O-acetyl-2,3-diazido-2,3-dideoxy-β-D-mannopyranosyl uronate)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 、 methyl 4-O-(methyl 4-O-acetyl-2,3-diazido-2,3-dideoxy-α-D-mannopyranosyl uronate)-2,3,6-tri-O-benzyl-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