benzyl (R)-tetrahydrofuran-2-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (R)-tetrahydrofuran-2-carboxylate
• 英文别名: (R)-benzyl tetrahydrofuran-2-carboxylate；benzyl (2R)-oxolane-2-carboxylate
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: BDLCAVORXGWRJK-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (R)-tetrahydrofuran-2-carboxylate 在 草酰氯 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 zinc(II) chloride 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 32.0h， 生成
  参考文献：
  名称：

  Discovery of a novel series of indolinylpyrimidine-based GPR119 agonists: Elimination of ether-a-go-go-related gene liability using a hydrogen bond acceptor-focused approach

  摘要：

  DOI：

  10.1016/j.bmc.2021.116034
• 作为产物：
  描述：

  (S)-四氢呋喃-2-甲酸 、 苯甲醇 在 草酰氯 、 吡啶 作用下， 以 乙醚 为溶剂， 反应 22.0h， 生成 benzyl (R)-tetrahydrofuran-2-carboxylate
  参考文献：
  名称：

  Discovery of a novel series of indolinylpyrimidine-based GPR119 agonists: Elimination of ether-a-go-go-related gene liability using a hydrogen bond acceptor-focused approach

  摘要：

  DOI：

  10.1016/j.bmc.2021.116034

文献信息

• A scalable chemoenzymatic preparation of (R)-tetrahydrofuran-2-carboxylic acid
  作者：Yoshito Fujima、Yoshihiro Hirayama、Masaya Ikunaka、Yukifumi Nishimoto

  DOI：10.1016/s0957-4166(03)00249-0

  日期：2003.5

  To develop a practical scalable approach to (R)-tetrahydrofuran-2-carboxylic acid (THFC) 1, a chiral building block for furopenem. 2, enantioselective hydrolysis of its esters is explored: When ethyl (+/-)-tetrahydrofuran-2-carboxylate 3d (2 M, 288 g/L) is digested by an Aspergillus melleus protease 0.2% (w/v)} in a 1.5 M potassium phosphate buffer (pH 8) for 20 h, enantioselective hydrolysis proceeds with E=60 to give (R)-THFC 1 in 94.4% ee. On separation from the left-over antipodal ester (S)-3d by partition, (R)-THFC 1 is treated with N,N-dicyclohexylamine (DCHA) in methyl ethyl ketone/methanol (5:1) to precipitate the crystalline salt 4 that contains (R)-THFC 1 of >99% ee in 22% overall yield from (+/-)-3d. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Enantioselective Copper-Catalyzed Intramolecular O−H Insertion: An Efficient Approach to Chiral 2-Carboxy Cyclic Ethers
  作者：Shou-Fei Zhu、Xiao-Guang Song、Yu Li、Yan Cai、Qi-Lin Zhou

  DOI：10.1021/ja1078464

  日期：2010.11.24

  A copper-catalyzed asymmetric intramolecular O-H insertion of omega-hydroxy-alpha-diazoesters has been accomplished by using chiral spiro bisoxazoline ligands. This highly enantioselective intramolecular O-H insertion reaction provides an efficient approach to a variety of synthetically important chiral 2-carboxy cyclic ethers with different ring sizes as well as substitution patterns.
• Discovery of a novel series of indolinylpyrimidine-based GPR119 agonists: Elimination of ether-a-go-go-related gene liability using a hydrogen bond acceptor-focused approach
  作者：Masahiro Kamaura、Osamu Kubo、Hiromichi Sugimoto、Naoyoshi Noguchi、Hirohisa Miyashita、Shinichi Abe、Kae Matsuda、Yoshiyuki Tsujihata、Tomoyuki Odani、Shinji Iwasaki、Toshiki Murata、Kenjiro Sato

  DOI：10.1016/j.bmc.2021.116034

  日期：2021.3