ethyl {[5-C-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran]-3-yl}carboxylate | 24877-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl {[5-C-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran]-3-yl}carboxylate
• 英文别名: ethyl 5-(3,4-dihydroxytetrahydrofuran-2-yl)-2-methylfuran-3-carboxylate；5-(1',4'-Anhydro-D-ribo-tetrahydroxybutyl)-2-methyl-3-furancarbonsaeure-ethylester；ethyl 5-[(2R,3R,4R)-3,4-dihydroxyoxolan-2-yl]-2-methylfuran-3-carboxylate
• CAS: 24877-25-6；35931-56-7；39679-86-2；106136-99-6；106137-00-2
• 化学式: C₁₂H₁₆O₆
• 分子量: 256.255
• InChiKey: XGUZSCVETPLQKH-IEBDPFPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  89.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl {[5-C-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran]-3-yl}carboxylate 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 生成 5-[5-C-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran-3-yl]-1,3,4-oxadiazole-2(3H)-thione
  参考文献：
  名称：

  带有取代的1,3,4-恶二唑的新C-呋喃糖苷的合成及抑菌活性

  摘要：

  从乙基2- [5-（3,4-二羟基四氢呋喃）开始合成带有C-呋喃糖苷部分的新2,5-二取代的1,3,4-恶二唑衍生物及其糖及其过O-乙酰基衍生物-2-基）-2-甲基呋喃-3-基] -2-氧代乙酸酯。使用乙酸酐对糖进行杂环化，得到了相应的恶二唑啉无环C-核苷。抗菌活性评估表明，许多合成的化合物均显示出中等至较高的抗菌活性。J.杂环化​​学。（2011）

  DOI：

  10.1002/jhet.679
• 作为产物：
  描述：

  L-(-)-葡萄糖 、 乙酰乙酸乙酯 在 indium(III) chloride 作用下， 以 水 为溶剂， 生成 ethyl {[5-C-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran]-3-yl}carboxylate
  参考文献：
  名称：

  带有取代的1,3,4-恶二唑的新C-呋喃糖苷的合成及抑菌活性

  摘要：

  从乙基2- [5-（3,4-二羟基四氢呋喃）开始合成带有C-呋喃糖苷部分的新2,5-二取代的1,3,4-恶二唑衍生物及其糖及其过O-乙酰基衍生物-2-基）-2-甲基呋喃-3-基] -2-氧代乙酸酯。使用乙酸酐对糖进行杂环化，得到了相应的恶二唑啉无环C-核苷。抗菌活性评估表明，许多合成的化合物均显示出中等至较高的抗菌活性。J.杂环化​​学。（2011）

  DOI：

  10.1002/jhet.679

文献信息

• Preparation of polyhydroxyalkyl- and C-glycosylfuran derivatives from free sugars catalyzed by cerium(III) chloride in aqueous solution: an improvement of the Garcia González reaction
  作者：Anup Kumar Misra、Geetanjali Agnihotri

  DOI：10.1016/j.carres.2004.02.011

  日期：2004.5

  Unprotected aldose sugars react smoothly with 1,3-diones or beta-ketoesters in the presence of CeCl(3).7H(2)O in aqueous solution to produce polyhydroxylalkyl- and C-glycosylfuran derivatives in excellent yield. Operationally simple, mild neutral reaction conditions in aqueous solution is the key feature of this methodology.

  在水溶液中存在CeCl（3）.7H（2）O的情况下，未保护的醛糖与1,3-二酮或β-酮酸酯的反应平稳，可产生高收率的多羟基烷基和C-糖基呋喃衍生物。在水溶液中操作简单，温和的中性反应条件是该方法的关键特征。
• Indium(III) Chloride/Water: A Versatile Catalytic System for the Synthesis of <i>C</i>-Furyl Glycosides and Trihydroxyalkyl Furan Derivatives
  作者：Jhillu Yadav、B. Reddy、Mende Sreenivas、G. Satheesh

  DOI：10.1055/s-2007-966056

  日期：2007.6

  Hexose sugars undergo smooth coupling with 1,3-diketones and β-keto esters in the presence of 10 mol% of indium(III) chloride in water at 80 °C to furnish C-furyl glycosides in excellent yields, whereas pentose sugars produce trihydroxyalkyl-substituted furan derivatives with high selectivity. The reactions of cyclic ketones such as cyclohexane-1,3-dione or dimedone with D-glucose in acetonitrile at

  己糖与 1,3-二酮和 β-酮酯在 10 mol% 氯化铟 (III) 的水中在 80 °C 存在下平滑偶联，以极好的产率提供 C-呋喃糖苷，而戊糖产生三羟基烷基-取代的呋喃衍生物具有高选择性。环己烷-1,3-二酮或二甲酮等环状酮与 D-葡萄糖在乙腈中于 80 °C 反应生成相应的四氢苯并呋喃糖苷衍生物。
• Iron(III) Chloride in Ethanol-Water: Highly Efficient Catalytic System for the Synthesis of Garcia Gonzalez Polyhydroxyalkyl- and C-Glycosylfurans
  作者：Lingaiah Nagarapu、Mahankhali Chary、Apuri Satyender、B. Supriya、Rajashaker Bantu

  DOI：10.1055/s-0029-1216865

  日期：2009.7

  An efficient method has been developed for the synthesis of Garcia Gonzalez polyhydroxyalkyl- and C-glycosylfurans in excellent yields from unprotected sugar aldoses with β-keto esters by Knoevenagel condensation in the presence of anhydrous iron(III) chloride. d-glucose - β-keto esters - Knoevenagel reaction - furans - carbohydrates

  在无水氯化铁（III）存在下，通过Knoevenagel缩合反应，由未保护的糖醛糖与β-酮酸酯以优异的产率合成了有效的加西亚·冈萨雷斯聚羟基烷基和C-糖基呋喃的有效方法。 d-葡萄糖-β-酮酯-Knoevenagel反应-呋喃-碳水化合物
• 5-(5-Aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate and New Cyclic C-Glycoside Analogues from Carbohydrate Precursors with MAO-B, Antimicrobial and Antifungal Activities
  作者：Mohamed Mohamed El-Sadek、Seham Yassen Hassan、Nagwa Said Abd El-Dayem、Galila Ahmed Yacout

  DOI：10.3390/molecules17067010

  日期：——

  Cyclization of acyclic C-glycoside derivatives 1a,b to 2a,b as the major isomers, and 4a,b as the minor isomers were carried out. The isopropylidene derivatives 3a,b were prepared, as well as the hydrazide derivative 6, which was condensed with a variety of aldehydes to give hydrazones 7a–e which were also prepared from the compounds 12a–e. Acetylation of 7a,d gave the corresponding acetyl derivatives 8a,d, respectively. In addition, the dicarbonyl compound 9 was prepared in the hydrate form, which reacted with a number of aroylhydrazines to give the corresponding bisaroyl-hydrazones 10a–d, which were cyclized into 1,3,4-oxadiazoles 11a–d. Furthermore, two of the prepared compounds were examined to show the ability to activate MAO-B. In addition a number of prepared compounds showed antibacterial and antiviral activities.

  将无环 C-糖苷衍生物 1a,b 环化成主要异构体 2a,b 和次要异构体 4a,b。制备出了异亚丙基衍生物 3a、b 以及酰肼衍生物 6，后者与多种醛缩合生成了酰肼 7a-e，这些酰肼也是由化合物 12a-e 制备而成的。对 7a,d 进行乙酰化处理后，可分别得到相应的乙酰基衍生物 8a,d。此外，还制备了水合物形式的二羰基化合物 9，该化合物与一些酰肼反应生成相应的双酰肼 10a-d，然后环化成 1,3,4-噁二唑 11a-d。此外，研究还发现其中两种化合物具有激活 MAO-B 的能力。此外，一些制备的化合物还显示出抗菌和抗病毒活性。
• Synthesis and antimicrobial activity of new C-furyl glycosides bearing substituted 1,3,4-oxadiazoles
  作者：Wael A. El-Sayed、Hebat-Allah S. Abbas、Ashraf M. Mohamed、Adel A.-H. Abdel-Rahman

  DOI：10.1002/jhet.679

  日期：2011.9

  New 2,5‐disubstituted 1,3,4‐oxadiazole derivatives bearing C‐furyl glycoside moieties and their sugar hydrazone as well as their per‐O‐acetyl derivatives were synthesized starting from ethyl 2‐[5‐(3,4‐dihydroxytetrahydrofuran‐2‐yl)‐2‐methylfuran‐3‐yl]‐2‐oxoacetate. Heterocyclization of the sugar hydrazones using acetic anhydride afforded the corresponding oxadiazoline acyclic C‐nucleosides. The antimicrobial

  从乙基2- [5-（3,4-二羟基四氢呋喃）开始合成带有C-呋喃糖苷部分的新2,5-二取代的1,3,4-恶二唑衍生物及其糖及其过O-乙酰基衍生物-2-基）-2-甲基呋喃-3-基] -2-氧代乙酸酯。使用乙酸酐对糖进行杂环化，得到了相应的恶二唑啉无环C-核苷。抗菌活性评估表明，许多合成的化合物均显示出中等至较高的抗菌活性。J.杂环化​​学。（2011）