1-[(2R,4S,5R)-4-[(4-methoxyphenyl)-diphenylmethoxy]-5-[[(2R,3S,5R)-2-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphinothioyloxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione | 146503-48-2

• 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-[(4-methoxyphenyl)-diphenylmethoxy]-5-[[(2R,3S,5R)-2-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphinothioyloxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 146503-48-2
• 化学式: C₆₀H₅₉N₄O₁₂PS
• 分子量: 1091.19
• InChiKey: NAFQLWQZEOXWOA-AHQRGNJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  78
• 可旋转键数：
  20
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  205
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-4-[(4-methoxyphenyl)-diphenylmethoxy]-5-[[(2R,3S,5R)-2-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphinothioyloxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 碘 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 1-[(2R,4S,5R)-5-[[fluoro-[(2R,3S,5R)-2-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphinothioyl]oxymethyl]-4-[(4-methoxyphenyl)-diphenylmethoxy]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  核苷二氟磷酸酯和核苷二氟硫代磷酸酯二酯的新条目

  摘要：

  在三乙胺三氢氟化物存在下，用碘氧化H-膦酸酯或H-膦酰硫代酸酯二酯，可以快速，定量地形成相应的氟代磷酸酯或硫代氟代磷酸酯二酯。

  DOI：

  10.1016/0040-4039(96)00606-5
• 作为产物：
  描述：

  3'-O-monomethoxytritylthymidine 、 5'-O-monomethoxytritylthymidine 3'-H-phosphonothioate 在 吡啶 、 三甲基乙酰氯 作用下， 生成 1-[(2R,4S,5R)-4-[(4-methoxyphenyl)-diphenylmethoxy]-5-[[(2R,3S,5R)-2-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphinothioyloxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 、 1-[(2R,4S,5R)-4-[(4-methoxyphenyl)-diphenylmethoxy]-5-[[(2R,3S,5R)-2-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphinothioyloxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Stereospecific oxidation and oxidative coupling of H-phosphonate and H-phosphonothioate diesters

  摘要：

  Oxidation of dinucleoside H-phosphonothioate diesters with the aid of iodine in aqueous acetonitrile and triethylamine, and oxidative coupling of H-phosphonate and H-phosphonothioate diesters with ethanol under similar conditions in anhydrous acetonitrile were found to be stereospecific reactions.

  DOI：

  10.1016/s0040-4039(00)79847-9

文献信息

• 3H-1,2-benzothiaselenol-3-one. A new selenizing reagent for nucleoside H-phosphonate and H-phosphonothioate diesters
  作者：Jacek Stawiński、Mats Thelin

  DOI：10.1016/s0040-4039(00)60887-0

  日期：1992.11

  A new selenium-transferring reagent, 3H-1,2-benzothiaselenol-3-one (1), has been developed for the conversion of nucleoside H-phosphonate and nucleoside H-phosphonothioate diesters into the corresponding seleno analogues. The reagent is soluble in common organic solvents and shows an enhanced rate of selenium transfer compared to elemental selenium or potassium selenocyanate. Selenization with the

  已经开发了一种新的硒转移试剂3 H -1,2-苯并硫代噻吩酚-3-酮（1），用于将核苷H-膦酸酯和核苷H-膦硫代酸酯二酯转化为相应的硒类似物。该试剂可溶于常见的有机溶剂，与元素硒或硒氰酸钾相比，硒的转移速率更高。试剂1的硒化是立体定向的，最有可能在磷中心保留构型而发生。
• Stereospecific oxidation and oxidative coupling of H-phosphonate and H-phosphonothioate diesters
  作者：Jacek Stawiński、Roger Strömberg、Rula Zain

  DOI：10.1016/s0040-4039(00)79847-9

  日期：1992.5

  Oxidation of dinucleoside H-phosphonothioate diesters with the aid of iodine in aqueous acetonitrile and triethylamine, and oxidative coupling of H-phosphonate and H-phosphonothioate diesters with ethanol under similar conditions in anhydrous acetonitrile were found to be stereospecific reactions.
• Bollmark, Martin; Zain, Rula; Stawinski, Jacek, Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S68 - S71
  作者：Bollmark, Martin、Zain, Rula、Stawinski, Jacek

  DOI：——

  日期：——
• Nucleoside H-phosphonates. 14. Synthesis of nucleoside phosphoroselenoates and phosphorothioselenoates via stereospecific selenization of the corresponding H-phosphonate and H-phosphonothioate diesters with the aid of new selenium-transfer reagent, 3H-1,2-benzothiaselenol-3-one
  作者：Jacek Stawinski、Mats Thelin

  DOI：10.1021/jo00080a021

  日期：1994.1

  An efficient conversion of nucleoside H-phosphonate and nucleoside H-phosphonothioate diesters into the corresponding phosphoroselenoates and phosphorothioselenoates was achieved with a new selenium-transferring reagent, 3M-1,2-benzothiaselenol-3-one (BTSe, 1). The reagent is soluble in common organic solvents and shows an enhanced rate of selenium transfer compared to elemental selenium or potassium selenocyanate. The reaction was found to be stereospecific and occurs with retention of configuration at the phosphorus center. BTSe also proved to be effective in the conversion of phosphite triesters into the corresponding phosphoroselenoates under reactions conditions which are compatible with both solution- and solid-phase synthesis of oligonucleotides.
• A new entry to nucleoside phosphorofluoridate and nucleoside phosphorofluoridothioate diesters
  作者：Martin Bollmark、Rula Zain、Jacek Stawiński

  DOI：10.1016/0040-4039(96)00606-5

  日期：1996.5

  Oxidation of H-phosphonate or H-phosphonothioate diesters with iodine in the presence of triethylamine trishydrofluoride furnished a rapid and quantitative formation of the corresponding phosphorofluoridate or phosphorofluoridothioate diesters.

  在三乙胺三氢氟化物存在下，用碘氧化H-膦酸酯或H-膦酰硫代酸酯二酯，可以快速，定量地形成相应的氟代磷酸酯或硫代氟代磷酸酯二酯。