(2S,3S)-[(2-benzyloxymethyl-5-oxotetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester | 651718-75-1

• 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]phosphonothioic acid O,O-diethyl ester
• 英文别名: [difluoro-[(2S,3S)-5-oxo-2-(phenylmethoxymethyl)oxolan-3-yl]methyl]-diethoxy-sulfidophosphanium
• CAS: 651718-75-1
• 化学式: C₁₇H₂₃F₂O₅PS
• 分子量: 408.403
• InChiKey: YBNKXSRWCKZWLL-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3S)-[(2-benzyloxymethyl-5-oxotetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester 在 palladium on activated charcoal 吡啶 、 2,6-二甲基吡啶 、 锂硼氢 、 硼酸三甲酯 、 偶氮二异丁腈 、 偶氮二甲酸二异丙酯 、 氢气 、 三正丁基氢锡 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 95.25h， 生成 diethyl (2R)-4-(6-chloro-9H-purin-9-yl)-2-{2-[(diethoxyphosphoryl)oxy]ethyl}-1,1-difluorobutylphosphonate
  参考文献：
  名称：

  Synthesis of acyclic nucleotide analogues possessing a difluoromethylene phosphonyl group at the side chain

  摘要：

  A synthetic approach to a new type of acyclic nucleotide analogues 8 and 9 was examined. The design was based on acyclic modification of MRS 2179, a P2Y(1)-antagonist, and replacement of one of two phosphate groups characterized by MRS 2179 with an isosteric difluoromethylenephosphonyl group. The nucleotide analogues 8 and 9 were enantio-divergently prepared as their ester-protecting derivatives from a highly differentiated 1,5-pentanediol derivative possessing a difluoromethylenephosphonyl group at the 3-position. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.064
• 作为产物：
  描述：

  tert-butyl (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate 在 劳森试剂 、 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 、 甲苯 、 Petroleum ether 为溶剂， 反应 15.33h， 生成 (2S,3S)-[(2-benzyloxymethyl-5-oxotetrahydrofuran-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

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.
• Synthesis of acyclic nucleotide analogues possessing a difluoromethylene phosphonyl group at the side chain
  作者：Tetsuo Murano、Yoko Yuasa、Hirokuni Kobayakawa、Tsutomu Yokomatsu、Shiroshi Shibuya

  DOI：10.1016/j.tet.2003.10.064

  日期：2003.12

  A synthetic approach to a new type of acyclic nucleotide analogues 8 and 9 was examined. The design was based on acyclic modification of MRS 2179, a P2Y(1)-antagonist, and replacement of one of two phosphate groups characterized by MRS 2179 with an isosteric difluoromethylenephosphonyl group. The nucleotide analogues 8 and 9 were enantio-divergently prepared as their ester-protecting derivatives from a highly differentiated 1,5-pentanediol derivative possessing a difluoromethylenephosphonyl group at the 3-position. (C) 2003 Elsevier Ltd. All rights reserved.