3-O-(5’,5’-diethoxycarbonylpentyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose | 1428727-55-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-O-(5’,5’-diethoxycarbonylpentyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: diethyl 2-[4-[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy]butyl]propanedioate
• CAS: 1428727-55-2
• 化学式: C₂₃H₃₈O₁₀
• 分子量: 474.549
• InChiKey: NKYQMWOTSRXGEL-ZIKOTGLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-(5’,5’-diethoxycarbonylpentyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 、 cisplatin 在 sodium hydroxide 、 silver nitrate 作用下， 以 水 为溶剂， 反应 52.0h， 生成 3-O-(5’,5’-dicarboxypentyl)-D-glucopyranose diammine platinum complex
  参考文献：
  名称：

  Formation of Glyco-Functionalized Platinum Complexes by Cross-Metathesis and Evaluation of Their Efficacy in Inhibition of Lung Tumor Cell Lines

  摘要：

  Syntheses of carbohydrate-functionalized platinum complexes resembling presently employed cytostatics were performed. Mono-allylated sugar substrates obtained in two steps from glucose and galactose were connected with 2-allyl diethyl malonate by cross-metathesis. Following hydrogenation and acidic cleavage of the ester and alkylidene functionalities gave dicarboxylated glycoconjugates, which were transformed into their diammine platinum complexes. The antitumor activities of these platinum complexes were checked by sensitivity testing with 11 lung cancer cell lines. The novel glucose-platinum complex proved to be comparable to the drug carboplatin.

  DOI：

  10.1080/07328303.2012.739231
• 作为产物：
  描述：

  双丙酮葡萄糖 在 Hoveyda-Grubbs catalyst second generation 、 palladium on activated charcoal 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 3-O-(5’,5’-diethoxycarbonylpentyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Formation of Glyco-Functionalized Platinum Complexes by Cross-Metathesis and Evaluation of Their Efficacy in Inhibition of Lung Tumor Cell Lines

  摘要：

  Syntheses of carbohydrate-functionalized platinum complexes resembling presently employed cytostatics were performed. Mono-allylated sugar substrates obtained in two steps from glucose and galactose were connected with 2-allyl diethyl malonate by cross-metathesis. Following hydrogenation and acidic cleavage of the ester and alkylidene functionalities gave dicarboxylated glycoconjugates, which were transformed into their diammine platinum complexes. The antitumor activities of these platinum complexes were checked by sensitivity testing with 11 lung cancer cell lines. The novel glucose-platinum complex proved to be comparable to the drug carboplatin.

  DOI：

  10.1080/07328303.2012.739231