1,6-Anhydro-4-deoxy-4-<(1S)-(1,4/2,3,5)-2,3,4-triacetoxy-5-(acetoxymethyl)-1-cyclohexylamino>-β-D-mannopyranose | 141232-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: 1,6-Anhydro-4-deoxy-4-<(1S)-(1,4/2,3,5)-2,3,4-triacetoxy-5-(acetoxymethyl)-1-cyclohexylamino>-β-D-mannopyranose
• CAS: 141232-08-8
• 化学式: C₂₅H₃₅NO₁₄
• 分子量: 573.551
• InChiKey: OMJLOPQATQFJEX-LJSXBTQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.69
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  188.29
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  1,6-Anhydro-4-deoxy-4-<(1S)-(1,4/2,3,5)-2,3,4-triacetoxy-5-(acetoxymethyl)-1-cyclohexylamino>-β-D-mannopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以55%的产率得到1,6-Anhydro-4-deoxy-4-<(1S)-(1,4/2,3,5)-2,3,4-trihydroxy-5-(hydroxymethyl)-1-cyclohexylamino>-β-D-mannopyranose
  参考文献：
  名称：

  Synthesis and enzyme-inhibitory activity of methyl acarviosin analogues having the α- manno configuration

  摘要：

  Two methyl acarviosin analogues 3a and 4a, having the alpha-manno configuration, and their dihydro derivatives 6a and 7a were synthesised by coupling the protected pseudo-sugar epoxides with methyl 4-amino-4-deoxy- and -4,6-dideoxy-alpha-D-mannopyranoside. Similarly, two analogous compounds 5a and 8a composed of the 1,6-anhydro-beta-D-mannopyranose residues were prepared. Compound 7a showed mild inhibitory activity against Jack bean alpha-D-mannosidase, and 3a was a moderate inhibitor of both alpha-D-mannosidase and yeast alpha-D-glucosidase.

  DOI：

  10.1016/0008-6215(92)84056-x
• 作为产物：
  描述：

  4-Amino-1,6-anhydro-4-deoxy-β-D-mannopyranose 、 乙酸酐 、 1,2-Anhydro-5a-carba-β-D-mannopyranose 在 吡啶 作用下， 生成 1,6-Anhydro-4-deoxy-4-<(1S)-(1,4/2,3,5)-2,3,4-triacetoxy-5-(acetoxymethyl)-1-cyclohexylamino>-β-D-mannopyranose
  参考文献：
  名称：

  Synthesis and enzyme-inhibitory activity of methyl acarviosin analogues having the α- manno configuration

  摘要：

  Two methyl acarviosin analogues 3a and 4a, having the alpha-manno configuration, and their dihydro derivatives 6a and 7a were synthesised by coupling the protected pseudo-sugar epoxides with methyl 4-amino-4-deoxy- and -4,6-dideoxy-alpha-D-mannopyranoside. Similarly, two analogous compounds 5a and 8a composed of the 1,6-anhydro-beta-D-mannopyranose residues were prepared. Compound 7a showed mild inhibitory activity against Jack bean alpha-D-mannosidase, and 3a was a moderate inhibitor of both alpha-D-mannosidase and yeast alpha-D-glucosidase.

  DOI：

  10.1016/0008-6215(92)84056-x