1,4-di-O-acetyl-2,6-di-O-benzyl-3-O-methyl-α-D-mannopyranose | 194594-70-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-di-O-acetyl-2,6-di-O-benzyl-3-O-methyl-α-D-mannopyranose
• CAS: 194594-70-2
• 化学式: C₂₅H₃₀O₈
• 分子量: 458.508
• InChiKey: KXJKKLLFWULUEQ-VAFBSOEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,4-di-O-acetyl-2,6-di-O-benzyl-3-O-methyl-α-D-mannopyranose 在 molecular sieve 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2R,3R,4S,5S,6R)-6-((2R,3R,4S,5S,6S)-6-Allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Synthesis of a Tetra- and a Hexasaccharide Donor Corresponding to the Non-Reducing Termini of Mycobacterial 3-O-Methylmannose Polysaccharide (MMP)

  摘要：

  The blockwise synthesis of the title compounds, namely the tetra-and the hexasaccharide trichloroacetimidates (20) and (23), is described. Both acetates and imidates were employed as glycosyl donors in most of the coupling reactions. As nearly all of the synthetic intermediates contain one or more OCH3 groups, they are easily identified by NMR spectroscopy the methyl signals. The fully functionalized compounds 20 and 23 correspond to the non-reducing terminal fragments of mycobacterial 3-O-methylmannose polysaccharide (MMP), and can serve as suitable building blocks for the synthesis of higher-order structures of MMP.

  DOI：

  10.1080/07328309708006545
• 作为产物：
  描述：

  乙酸酐 、 2,6-di-O-benzyl-3-O-methyl-D-mannopyranose 以 吡啶 为溶剂， 生成 1,4-di-O-acetyl-2,6-di-O-benzyl-3-O-methyl-α-D-mannopyranose
  参考文献：
  名称：

  Synthesis of a Tetra- and a Hexasaccharide Donor Corresponding to the Non-Reducing Termini of Mycobacterial 3-O-Methylmannose Polysaccharide (MMP)

  摘要：

  The blockwise synthesis of the title compounds, namely the tetra-and the hexasaccharide trichloroacetimidates (20) and (23), is described. Both acetates and imidates were employed as glycosyl donors in most of the coupling reactions. As nearly all of the synthetic intermediates contain one or more OCH3 groups, they are easily identified by NMR spectroscopy the methyl signals. The fully functionalized compounds 20 and 23 correspond to the non-reducing terminal fragments of mycobacterial 3-O-methylmannose polysaccharide (MMP), and can serve as suitable building blocks for the synthesis of higher-order structures of MMP.

  DOI：

  10.1080/07328309708006545