3-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)propaldehyde | 856668-30-9

• 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: 3-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)propaldehyde
• CAS: 856668-30-9
• 化学式: C₁₇H₂₄O₁₀
• 分子量: 388.372
• InChiKey: JEOCMJKTDUKFMV-UHDSXZAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  131.5
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)propaldehyde 、 甲基三苯基溴化膦 在 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以70%的产率得到Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-but-3-enyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  C-Linked Galactosyl Serine AFGP Analogues as Potent Recrystallization Inhibitors

  摘要：

  A series of C-linked antifreeze glycoprotein analogues have been prepared to evaluate antifreeze activity as a function of distance between the carbohydrate moiety and polypeptide backbone. The building blocks for these analogues were prepared using either an olefin cross-metathesis or catalytic asymmetric hydrogenation. Analysis of antifreeze protein-specific activity revealed that only analogue 2a (n = 1) was a potent recrystallization inhibitor and thus has potential medical and industrial applications.

  DOI：

  10.1021/ol050677x
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 硼烷 、 氢溴酸 、 六正丁基二锡 、 溶剂黄146 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 13.5h， 生成 3-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)propaldehyde
  参考文献：
  名称：

  C-Linked Galactosyl Serine AFGP Analogues as Potent Recrystallization Inhibitors

  摘要：

  A series of C-linked antifreeze glycoprotein analogues have been prepared to evaluate antifreeze activity as a function of distance between the carbohydrate moiety and polypeptide backbone. The building blocks for these analogues were prepared using either an olefin cross-metathesis or catalytic asymmetric hydrogenation. Analysis of antifreeze protein-specific activity revealed that only analogue 2a (n = 1) was a potent recrystallization inhibitor and thus has potential medical and industrial applications.

  DOI：

  10.1021/ol050677x