(5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole | 20746-63-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 20746-63-8
• 化学式: C₁₅H₂₄O₆
• 分子量: 300.352
• InChiKey: XVJPYQDFXZAPEI-HENWMNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole 在 Hoveyda-Grubbs catalyst second generation 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 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
• 作为产物：
  描述：

  3-溴丙烯 、 双丙酮葡萄糖 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 16.0h， 以66%的产率得到(5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
  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

文献信息

• H2SO4-silica-promoted ‘on-column’ removal of benzylidene, isopropylidene, trityl and tert-butyldimethylsilyl groups
  作者：Bimalendu Roy、Priya Verma、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2008.10.003

  日期：2009.1

  H2SO4-silica-promoted removal of benzylidene, isopropylidene, trityl and tert-butyldimethylsilyl groups from sugar derivatives was accomplished by following an 'on-column' Protocol in a virtually waste-free condition. (C) 2008 Elsevier Ltd. All rights reserved.
• Formation of Glyco-Functionalized Platinum Complexes by Cross-Metathesis and Evaluation of Their Efficacy in Inhibition of Lung Tumor Cell Lines
  作者：Janina Möker、Ursula Salge-Bartels、Joachim Thiem

  DOI：10.1080/07328303.2012.739231

  日期：2012.11

  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.