1-(4-chloro-4-deoxy-β-D-galactopyranosyl)propan-2-one | 945622-29-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-chloro-4-deoxy-β-D-galactopyranosyl)propan-2-one
• 英文别名: 1-[(2S,3R,4R,5R,6R)-5-chloro-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]propan-2-one
• CAS: 945622-29-7
• 化学式: C₉H₁₅ClO₅
• 分子量: 238.668
• InChiKey: IOTVANJNWXAMRQ-BGKGJTHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-chloro-4-deoxy-β-D-galactopyranosyl)propan-2-one 在 吡啶 、 4-二甲氨基吡啶 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 1-(2'-acetyl-4'-chloro-4'-deoxy-β-D-galactopyranosyl)propan-2-one-3',6'-ketal
  参考文献：
  名称：

  Synthesis of Novel Caged Intramolecular Ketals of β‐C‐Glycopyranosidic Ketones

  摘要：

  Novel caged intramolecular ketals of beta-C-glycosidic ketones were prepared from pyranoses. The structures of the new compounds were elucidated by NMR and HRMS spectral analysis. Preliminary studies revealed that the intramolecular ketal could be used to protect 3- and 6- hydroxyl groups of beta-C-glycosidic ketones.

  DOI：

  10.1080/07328300701609111
• 作为产物：
  描述：

  乙酰丙酮 、 4-氯-4-脱氧-Α-D-吡喃半乳糖 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 8.0h， 以94%的产率得到1-(4-chloro-4-deoxy-β-D-galactopyranosyl)propan-2-one
  参考文献：
  名称：

  Synthesis of Novel Caged Intramolecular Ketals of β‐C‐Glycopyranosidic Ketones

  摘要：

  Novel caged intramolecular ketals of beta-C-glycosidic ketones were prepared from pyranoses. The structures of the new compounds were elucidated by NMR and HRMS spectral analysis. Preliminary studies revealed that the intramolecular ketal could be used to protect 3- and 6- hydroxyl groups of beta-C-glycosidic ketones.

  DOI：

  10.1080/07328300701609111

文献信息

• Synthesis and Biological Evaluation of Andrographolide C-Glycoside Derivatives as α-Glycosidase Inhibitors
  作者：Lin Yan、Haiwei Xu、Fengwu Liu、Jin Zhao、Hongmin Liu

  DOI：10.1002/cjoc.201100179

  日期：2012.4

  A series of new andrographolide C‐glycoside derivatives were synthesized by a facile route. The new compounds showed higher potency than the parent andrographolide evaluated as α‐glycosidase inhibitors in the preliminary study.

  通过一种简便的途径合成了一系列新的穿心莲内酯C-糖苷衍生物。与初步研究中被评估为α-糖苷酶抑制剂的母体穿心莲内酯相比，新化合物显示出更高的效价。
• Synthesis of Novel Caged Intramolecular Ketals of β‐<i>C</i>‐Glycopyranosidic Ketones
  作者：Lin Yan、Feng‐Wu Liu、Jian‐Li Yang、Hong‐Min Liu

  DOI：10.1080/07328300701609111

  日期：2007.9

  Novel caged intramolecular ketals of beta-C-glycosidic ketones were prepared from pyranoses. The structures of the new compounds were elucidated by NMR and HRMS spectral analysis. Preliminary studies revealed that the intramolecular ketal could be used to protect 3- and 6- hydroxyl groups of beta-C-glycosidic ketones.