[(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-hydroxyphosphinothioyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate | 124753-38-4

• 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: [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-hydroxyphosphinothioyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate
• CAS: 124753-38-4
• 化学式: C₄₈H₄₉N₄O₁₄PS
• 分子量: 968.975
• InChiKey: HPTNULYDQZQSMK-QAURSCKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  68.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  220.86
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  胸苷3'-苯甲酸酯 在 sulfur 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 正丁胺 作用下， 以 吡啶 为溶剂， 反应 1.0h， 生成 [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-hydroxyphosphinothioyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate
  参考文献：
  名称：

  酰基膦酸酯：通过酰基膦酸酯中间体立体定向和立体选择性生成二脱氧核糖核苷硫代磷酸酯的新方法

  摘要：

  通过二脱氧核糖核苷2,2,2-三氯乙氧基羰基膦酸酯和芳酰基膦酸酯通过新方法合成了脱氧核糖核苷硫代磷酸酯。通过用Me 3 SiCl-Zn-乙酰丙酮处理，将双脱氧核糖核苷2,2,2-三氯乙氧基羰基膦酸酯转化为双脱氧核糖核苷三甲基甲硅烷基亚磷酸酯，在磷处具有保留构型。通过用硫原位处理将亚磷酸甲硅烷基酯中间体转化为硫代磷酸酯。通过n-BuNH 2的作用，很容易将芳酰基从8-11上除去，并通过单质硫处理原位转化为双脱氧核糖核苷硫代磷酸酯中的仅一种非对映异构体（Rp-构型）。

  DOI：

  10.1016/s0040-4020(01)81630-6

文献信息

• Nucleoside Phosphite,<i>O</i>-Bis(1,1,1,3,3,3-hexafluoro-2-propyl) Deoxyribonucleosid-3′-yl Phosphites. A Versatile Synthetic Intermediate for Phosphonate Modified Nucleotide and Oligonucleotide Synthesis
  作者：Hideo Hosaka、Hiroyuki Nakamura、Hidenori Funakoshi、Hiroshi Takaku

  DOI：10.1246/cl.1992.935

  日期：1992.6

  The O-bis(1,1,1,3,3,3-hexa-fluoro-2-propyl) deoxyribonucleosid-3′-yl phosphite units could be converted into the O-nucleosid-3′-yl phosphonate, O-2-cyanoethyl O-nucleosid-3′-yl phosphonate, and O-1,1,1,3,3,3-hexafluoro-2-propyl O-nucleosid-3′-yl phosphonothioate. The phosphite unit reacted with 3′-O-benzoylthymidine in the presence of MeIm to give the dithymidylate derivatives.

  O-bis(1,1,1,3,3,3-六氟-2-丙基)脱氧核糖核苷-3′-基磷酸酯单元可以转化为O-核糖核苷-3′-基磷酸酯、O-2-氰乙基O-核糖核苷-3′-基磷酸酯和O-1,1,1,3,3,3-六氟-2-丙基O-核糖核苷-3′-基磷酸硫酸酯。在MeIm存在下，磷酸酯单元与3′-O-苯甲酰胸苷反应生成双胸苷酸衍生物。
• Nucleoside H-phosphonates. 13. Studies on 3H-1,2-benzodithiol-3-one derivatives as sulfurizing reagents for H-phosphonate and H-phosphonothioate diesters
  作者：Jacek Stawinski、Mats Thelin

  DOI：10.1021/jo00017a033

  日期：1991.8

  Formation of O-oxidized products during sulfurization of H-phosphonothioate and H-phosphonate diesters with 3H-1,2-benzodithiol-3-one 1,1-dioxide (1) was found to be due to generation of the O-oxidizing agents, most likely 3H-2,1-benzoxathiol-3-one 1-oxide (4) and 3H-2,1-benzoxathiol-3-one (5), during the course of the reactions. Another source of the side products formation may be the disproportionation of 1 that occurs in the presence of triethylamine. To overcome these problems, a new sulfur-transferring reagent, 3H-1,2-benzodithiol-3-one (3), has been developed. Under aqueous reaction conditions, which are compatible with both solution- and solid-phase synthesis of oligonucleotides, the reagent 3 furnished clean and fast conversion of H-phosphonothioate and H-phosphonate diesters into the corresponding phosphorodi- and phosphoromonothioates.
• STAWINSKI, JACEK;THELIN, MATS;ZAIN, RULA, TETRAHEDRON LETT., 30,(1989) N6, C. 2157-2160
  作者：STAWINSKI, JACEK、THELIN, MATS、ZAIN, RULA

  DOI：——

  日期：——
• FUJII, MITSUO;OZAKI, KOUJI;SEKINE, MITSUO;HATA, TSUJIAKI, TETRAHEDRON, 43,(1987) N 15, 3395-3407
  作者：FUJII, MITSUO、OZAKI, KOUJI、SEKINE, MITSUO、HATA, TSUJIAKI

  DOI：——

  日期：——