(2R,3S,4S,5R)-4-Benzoyloxy-3-fluoro-5-methoxy-tetrahydro-furan-2-carboxylic acid methyl ester | 551929-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R)-4-Benzoyloxy-3-fluoro-5-methoxy-tetrahydro-furan-2-carboxylic acid methyl ester
• CAS: 551929-64-7
• 化学式: C₁₄H₁₅FO₆
• 分子量: 298.268
• InChiKey: KFQMLDPZKFSSEB-FBKDDSFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R)-4-Benzoyloxy-3-fluoro-5-methoxy-tetrahydro-furan-2-carboxylic acid methyl ester 在 三氟甲磺酸三甲基硅酯 、 硫酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 0.57h， 生成
  参考文献：
  名称：

  Design, synthesis and binding affinity of 3′-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands

  摘要：

  Several 3'-fluoro analogues, la, 1b, and le of selective and potent adenosine A(3) receptor agonist, Cl-IB-MECA were synthesized from D-xylose via highly regioselective opening of lyxo-epoxides, 8a and 811 with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A(3) adenosine receptor, the corresponding 3-fluoro derivative showed remarkably decreased binding affinity, indicating that 3'-hydroxyl group acts as hydrogen bonding acceptor, not hydrogen bonding donor like fluorine atom in binding to the A(3) adenosine receptor. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00027-1
• 作为产物：
  描述：

  methyl-[O³,O⁵-isopropylidene-O²-(toluene-4-sulfonyl)-β-D-xylofuranoside] 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 ruthenium trichloride 、 sodium periodate 、 potassium hydrogen bifluoride 、 18-冠醚-6 、 四丁基氟化铵 、 sodium methylate 、 sodium fluoride 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 乙二醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 138.0h， 生成 (2R,3S,4S,5R)-4-Benzoyloxy-3-fluoro-5-methoxy-tetrahydro-furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Design, synthesis and binding affinity of 3′-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands

  摘要：

  Several 3'-fluoro analogues, la, 1b, and le of selective and potent adenosine A(3) receptor agonist, Cl-IB-MECA were synthesized from D-xylose via highly regioselective opening of lyxo-epoxides, 8a and 811 with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A(3) adenosine receptor, the corresponding 3-fluoro derivative showed remarkably decreased binding affinity, indicating that 3'-hydroxyl group acts as hydrogen bonding acceptor, not hydrogen bonding donor like fluorine atom in binding to the A(3) adenosine receptor. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00027-1

文献信息

• Design and Synthesis of A₃Adenosine Receptor Ligands, 3′-Fluoro Analogues of Cl-IB-MECA
  作者：Hea Ok Kim、Moo Hong Lim、Jae Gyu Park、Hyung Ryong Moon、Kenneth A. Jacobson、Hee-Doo Kim、Moon Woo Chun、Lak Shin Jeong

  DOI：10.1081/ncn-120022701

  日期：2003.10

  Synthesis of 3'-deoxy-3'-fluoro-N-6-substituted adenosines as bioisosteres of Cl-IB-MECA and their binding affinities to A(3) adenosine receptor are described.