phenyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside | 1319717-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: phenyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside
• 英文别名: (2R,4aR,6S,7S,8R,8aS)-7,8-diazido-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 1319717-02-6
• 化学式: C₁₉H₁₈N₆O₃S
• 分子量: 410.456
• InChiKey: LAHJFDYJFTWMIY-RRQVMCLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside 在 三叔丁基膦 、 二苯基亚砜 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 methyl 6-O-(2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-β-D-mannopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 、 methyl 6-O-(2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranosyl)-2,3,4-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
• 作为产物：
  描述：

  acetyl 4,6-di-O-acetyl-2,3-diazido-2,3-dideoxy-D-mannopyranoside 在 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 6.5h， 生成 phenyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside
  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