Methyl 2,3,6-tri-O-acetyl-4-deoxy-4-<(1S)-(1,4/5,6)-4,5,6-triacetoxy-3-(benzoyloxymethyl)-2-cyclohexen-1-ylamino>-α-D-mannopyranoside | 141232-09-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methyl 2,3,6-tri-O-acetyl-4-deoxy-4-<(1S)-(1,4/5,6)-4,5,6-triacetoxy-3-(benzoyloxymethyl)-2-cyclohexen-1-ylamino>-α-D-mannopyranoside
• CAS: 141232-09-9
• 化学式: C₃₃H₄₁NO₁₆
• 分子量: 707.686
• InChiKey: KNZSWIKXECGLHW-GORCUGTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  50.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  214.59
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  Methyl 2,3,6-tri-O-acetyl-4-deoxy-4-<(1S)-(1,4/5,6)-4,5,6-triacetoxy-3-(benzoyloxymethyl)-2-cyclohexen-1-ylamino>-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以64%的产率得到Methyl 4-deoxy-4-<(1S)-(1,4/2,3,5)-2,3,4-trihydroxy-5-(hydroxymethyl)-2-cyclohexen-1-ylamino>-α-D-mannopyranoside
  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：

  Methyl 4-acetamido-2,3,6-tri-O-acetyl-4-deoxy-α-D-mannopyranoside 在 吡啶 、 一水合肼 作用下， 反应 0.5h， 生成 Methyl 2,3,6-tri-O-acetyl-4-deoxy-4-<(1S)-(1,4/5,6)-4,5,6-triacetoxy-3-(benzoyloxymethyl)-2-cyclohexen-1-ylamino>-α-D-mannopyranoside
  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