(2S,3S)-[(2-benzyloxymethyl-5-oxotetrahydrofuran-3-yl)difluoromethyl]phosphonic acid diethyl ester | 675147-49-6

• 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: (2S,3S)-[(2-benzyloxymethyl-5-oxotetrahydrofuran-3-yl)difluoromethyl]phosphonic acid diethyl ester
• CAS: 675147-49-6
• 化学式: C₁₇H₂₃F₂O₆P
• 分子量: 392.337
• InChiKey: GXWQEZPIAYCZIR-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  (2S,3S)-[(2-benzyloxymethyl-5-oxotetrahydrofuran-3-yl)difluoromethyl]phosphonic acid diethyl ester 在 劳森试剂 、 硝酸铵 、 N,O-双三甲硅基乙酰胺 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 3.0h， 生成 (2S,3S,5S)-{[5-(6-benzoylaminopurin-9-yl)-2-benzyloxymethyltetrahydrofuran-3-yl]difluoromethyl}phosphonothioic acid O,O-diethyl ester
  参考文献：
  名称：

  N-Glycosylation of 2,3-dideoxyfuranose derivatives having a (diethoxyphosphorothioyl)difluoromethyl group at the 3α-position

  摘要：

  Lewis acid-mediated N-glycosylation of 2,3-dideoxyribofunanosides having a (diethoxyphosphorothioyl)difluoromethyl group at the 3alpha-position with silylated nucleobases was examined. The phosphorothioyldifluoromethyl was found to be an effective functional group for the diastereoselective synthesis of beta-N-1-pyrimidine-nucleotide analogues 26 and 28-30. However, the method was not useful for the diastereoselective synthesis of adenine nucleotide analogues. The nucleotide analogue 26 was transformed to the difluoromethylene-phosphonate analogue 31 of thymidine-3'-phosphate by oxidation with m-CPBA, followed by aqueous. work-up. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.069
• 作为产物：
  描述：

  tert-butyl (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate 在 盐酸 、 三氟甲磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 Petroleum ether 为溶剂， 反应 15.33h， 生成 (2S,3S)-[(2-benzyloxymethyl-5-oxotetrahydrofuran-3-yl)difluoromethyl]phosphonic acid diethyl ester
  参考文献：
  名称：

  N-Glycosylation of 2,3-dideoxyfuranose derivatives having a (diethoxyphosphorothioyl)difluoromethyl group at the 3α-position

  摘要：

  Lewis acid-mediated N-glycosylation of 2,3-dideoxyribofunanosides having a (diethoxyphosphorothioyl)difluoromethyl group at the 3alpha-position with silylated nucleobases was examined. The phosphorothioyldifluoromethyl was found to be an effective functional group for the diastereoselective synthesis of beta-N-1-pyrimidine-nucleotide analogues 26 and 28-30. However, the method was not useful for the diastereoselective synthesis of adenine nucleotide analogues. The nucleotide analogue 26 was transformed to the difluoromethylene-phosphonate analogue 31 of thymidine-3'-phosphate by oxidation with m-CPBA, followed by aqueous. work-up. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.069