1-[(2R,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-pyridin-2-ylphosphinothioyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione | 666736-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-[(2R,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-pyridin-2-ylphosphinothioyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 666736-51-2
• 化学式: C₆₇H₆₆N₅O₁₄PS
• 分子量: 1228.33
• InChiKey: VVGHWBNIVAHHHD-WVJJEIKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  88
• 可旋转键数：
  23
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  236
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-pyridin-2-ylphosphinothioyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 溶剂黄146 作用下， 以80%的产率得到1-[(2R,4S,5R)-4-hydroxy-5-[[[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-pyridin-2-ylphosphinothioyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Nucleoside H-phosphonates. Part 19: Efficient entry to novel nucleotide analogues with 2-pyridyl- and 4-pyridylphosphonothioate internucleotide linkages

  摘要：

  Synthetic and P-31 NMR spectroscopy studies resulted in the development of efficient protocols for the stereospecific synthesis of a novel type of nucleotide analogues, 2-pyridyl- and 4-pyridylphosphonothioates. The underlying chemistry involves formation of the P-C bond via a base-promoted reaction of suitably protected dithymidine H-phosphonothioates with N-methoxypyridinium tosylate in acetonitrile, or with trityl chloride in pyridine, to produce high yields of nucleotide analogues with a 2-pyridyl- or 4-pyridyl moiety directly bound to the phosphorus centre. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.010
• 作为产物：
  描述：

  N-methoxypyridinium tosylate 、 1-[(2R,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphinothioyloxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以80%的产率得到1-[(2R,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-pyridin-2-ylphosphinothioyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Nucleoside H-phosphonates. Part 19: Efficient entry to novel nucleotide analogues with 2-pyridyl- and 4-pyridylphosphonothioate internucleotide linkages

  摘要：

  Synthetic and P-31 NMR spectroscopy studies resulted in the development of efficient protocols for the stereospecific synthesis of a novel type of nucleotide analogues, 2-pyridyl- and 4-pyridylphosphonothioates. The underlying chemistry involves formation of the P-C bond via a base-promoted reaction of suitably protected dithymidine H-phosphonothioates with N-methoxypyridinium tosylate in acetonitrile, or with trityl chloride in pyridine, to produce high yields of nucleotide analogues with a 2-pyridyl- or 4-pyridyl moiety directly bound to the phosphorus centre. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.010

文献信息

• Nucleoside H-phosphonates. Part 19: Efficient entry to novel nucleotide analogues with 2-pyridyl- and 4-pyridylphosphonothioate internucleotide linkages
  作者：Tommy Johansson、Jacek Stawinski

  DOI：10.1016/j.tet.2003.11.010

  日期：2004.1

  Synthetic and P-31 NMR spectroscopy studies resulted in the development of efficient protocols for the stereospecific synthesis of a novel type of nucleotide analogues, 2-pyridyl- and 4-pyridylphosphonothioates. The underlying chemistry involves formation of the P-C bond via a base-promoted reaction of suitably protected dithymidine H-phosphonothioates with N-methoxypyridinium tosylate in acetonitrile, or with trityl chloride in pyridine, to produce high yields of nucleotide analogues with a 2-pyridyl- or 4-pyridyl moiety directly bound to the phosphorus centre. (C) 2003 Elsevier Ltd. All rights reserved.