benzoic acid (2S,3S,5S)-3-[(diethoxythiophosphoryl)difluoromethyl]-5-ethoxytetrahydrofuran-2-ylmethyl ester | 675147-66-7

• 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: benzoic acid (2S,3S,5S)-3-[(diethoxythiophosphoryl)difluoromethyl]-5-ethoxytetrahydrofuran-2-ylmethyl ester
• 英文别名: [[(2S,3S,5S)-2-(benzoyloxymethyl)-5-ethoxyoxolan-3-yl]-difluoromethyl]-diethoxy-sulfidophosphanium
• CAS: 675147-66-7
• 化学式: C₁₉H₂₇F₂O₆PS
• 分子量: 452.456
• InChiKey: UADITAMYRWBXBQ-BBWFWOEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 、 benzoic acid (2S,3S,5S)-3-[(diethoxythiophosphoryl)difluoromethyl]-5-ethoxytetrahydrofuran-2-ylmethyl ester 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到benzoic acid (2S,3S)-3-[(diethoxythiophosphoryl)difluoromethyl]-5-(5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-ylmethyl 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：

  (2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-ethoxytetrahydrofuran-3-yl]difluoromethyl}phosphonothioic acid O,O-diethyl ester 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 benzoic acid (2S,3S,5S)-3-[(diethoxythiophosphoryl)difluoromethyl]-5-ethoxytetrahydrofuran-2-ylmethyl 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

文献信息

• N-Glycosylation of 2,3-dideoxyfuranose derivatives having a (diethoxyphosphorothioyl)difluoromethyl group at the 3α-position
  作者：Tetsuo Murano、Yoko Yuasa、Soichiro Muroyama、Tsutomu Yokomatsu、Shiroshi Shibuya

  DOI：10.1016/j.tet.2003.09.069

  日期：2003.11

  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.