Butyric acid (R)-1-furo[2,3-c]pyridin-5-yl-ethyl ester | 185221-55-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡啶类
• 英文名称: Butyric acid (R)-1-furo[2,3-c]pyridin-5-yl-ethyl ester
• 英文别名: [(1R)-1-furo[2,3-c]pyridin-5-ylethyl] butanoate
• CAS: 185221-55-0
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: WSHAOJQUOSBXSU-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Butyric acid (R)-1-furo[2,3-c]pyridin-5-yl-ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以89%的产率得到(R)-1-(furo[2,3-c]pyridin-5-yl)ethanol
  参考文献：
  名称：

  Stereoselective Synthesis of Furo[2,3-c]pyridine Pyrimidine Thioethers, A New Class of Potent HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  An efficient stereoselective total synthesis of the furo[2,3-c]pyridine thiopyrimidine HIV-1 reverse transcriptase inhibitors, PNU-142721 and PNU-109886, has been developed. A convergent approach was utilized, providing direct access to the desired (S)-configuration of the molecule by making use of the alkylation of 4-amino-6-chloro-2-thiopyrimidine with the appropriate (R)-1-chloroethyl furo[2,3-c]pyridine intermediates. The successful preparation makes use of an efficient enzymatic kinetic resolution of the key 1-hydroxyethyl furo[2,3-c]pyridine intermediates to establish stereochemical control of the respective stereogenic centers. In addition, a workable asymmetric reduction strategy was developed for the synthesis of PNU-109886. Prudent reagent selection for the chlorination required for the final coupling reactions allowed for maintenance of the stereochemical integrity of the target compounds. Structural assignment of the absolute configuration of PNU-142721 and PNU-109886 as the (S)-enantiomer was confirmed by X-ray crystallographic analysis.

  DOI：

  10.1021/jo9810359
• 作为产物：
  描述：

  2-chloro-3-hydroxy-6-(1-hydroxyethyl)-pyridine 在 palladium hydroxide - carbon bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 、 正丁酸2,2,2-三氟乙酯 、 porcine pancreatic lipase type 、 碘 、 potassium carbonate 、 三乙胺 、 环己烯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 氯仿 、 水 为溶剂， 反应 229.0h， 生成 Butyric acid (R)-1-furo[2,3-c]pyridin-5-yl-ethyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Furo[2,3-c]pyridine Pyrimidine Thioethers, A New Class of Potent HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  An efficient stereoselective total synthesis of the furo[2,3-c]pyridine thiopyrimidine HIV-1 reverse transcriptase inhibitors, PNU-142721 and PNU-109886, has been developed. A convergent approach was utilized, providing direct access to the desired (S)-configuration of the molecule by making use of the alkylation of 4-amino-6-chloro-2-thiopyrimidine with the appropriate (R)-1-chloroethyl furo[2,3-c]pyridine intermediates. The successful preparation makes use of an efficient enzymatic kinetic resolution of the key 1-hydroxyethyl furo[2,3-c]pyridine intermediates to establish stereochemical control of the respective stereogenic centers. In addition, a workable asymmetric reduction strategy was developed for the synthesis of PNU-109886. Prudent reagent selection for the chlorination required for the final coupling reactions allowed for maintenance of the stereochemical integrity of the target compounds. Structural assignment of the absolute configuration of PNU-142721 and PNU-109886 as the (S)-enantiomer was confirmed by X-ray crystallographic analysis.

  DOI：

  10.1021/jo9810359

文献信息

• Stereoselective Synthesis of Furo[2,3-<i>c</i>]pyridine Pyrimidine Thioethers, A New Class of Potent HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors
  作者：Donn G. Wishka、David R. Graber、Eric P. Seest、Lester A. Dolak、Fusen Han、William Watt、Joel Morris

  DOI：10.1021/jo9810359

  日期：1998.10.1

  An efficient stereoselective total synthesis of the furo[2,3-c]pyridine thiopyrimidine HIV-1 reverse transcriptase inhibitors, PNU-142721 and PNU-109886, has been developed. A convergent approach was utilized, providing direct access to the desired (S)-configuration of the molecule by making use of the alkylation of 4-amino-6-chloro-2-thiopyrimidine with the appropriate (R)-1-chloroethyl furo[2,3-c]pyridine intermediates. The successful preparation makes use of an efficient enzymatic kinetic resolution of the key 1-hydroxyethyl furo[2,3-c]pyridine intermediates to establish stereochemical control of the respective stereogenic centers. In addition, a workable asymmetric reduction strategy was developed for the synthesis of PNU-109886. Prudent reagent selection for the chlorination required for the final coupling reactions allowed for maintenance of the stereochemical integrity of the target compounds. Structural assignment of the absolute configuration of PNU-142721 and PNU-109886 as the (S)-enantiomer was confirmed by X-ray crystallographic analysis.