methyl 3,4-anhydro-α-D-talohexopyranoside | 141231-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: methyl 3,4-anhydro-α-D-talohexopyranoside
• 英文别名: Methyl 3,4-anhydro-alpha-d-talohexopyranoside；(1S,2R,4S,5S,6R)-2-(hydroxymethyl)-4-methoxy-3,7-dioxabicyclo[4.1.0]heptan-5-ol
• CAS: 141231-97-2
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: RMWRLUMRRZLOGH-PZRMXXKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3,4-anhydro-α-D-talohexopyranoside 、 2,2-二甲氧基丙烷 生成 methyl 4-azido-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside 、 methyl 3-azido-3-deoxy-4,6-O-isopropylidene-α-D-idopyranoside
  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 2,3,6-tri-O-benzoyl-4-O-methanesulfonyl-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以87%的产率得到methyl 3,4-anhydro-α-D-talohexopyranoside
  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

文献信息

• Synthesis and enzyme-inhibitory activity of methyl acarviosin analogues having the α- manno configuration
  作者：Seiichiro Ogawa、Yoshikazu Nakamura

  DOI：10.1016/0008-6215(92)84056-x

  日期：1992.3

  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.