p-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl phosphonate | 157793-52-7

• 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: p-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl phosphonate
• 英文别名: 4-Chlorophenyl 5'-O-dimethoxytritylthymidin-3'-yl phosphonate；1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-(4-chlorophenoxy)phosphonoyloxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 157793-52-7
• 化学式: C₃₇H₃₆ClN₂O₉P
• 分子量: 719.128
• InChiKey: QMSCWKCGSXUGEN-LBFZIJHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  50
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  p-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl phosphonate 以 吡啶 为溶剂， 生成 保护胸苷
  参考文献：
  名称：

  Sobkowski, Michal; Stawinski, Jacek; Sobkowska, Anna, Journal of the Chemical Society. Perkin transactions I, 1994, # 13, p. 1803 - 1808

  摘要：

  DOI：
• 作为产物：
  描述：

  保护胸苷 、 triethylammonium 4-clorophenyl H-phosphonate 在 吡啶 、 三甲基乙酰氯 作用下， 反应 0.5h， 生成 p-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl phosphonate
  参考文献：
  名称：

  芳基氢膦酸铵在制备核苷氢膦酸结构单元中的用途

  摘要：

  使用4-甲基苯基H-膦酸铵4c将5'- O-（二甲氧基三苯甲基）-2'-脱氧核苷衍生物6转化为相应的3'- H-膦酸酯2，并以高纯度分离得到。高产。

  DOI：

  10.1016/0040-4039(96)01993-4

文献信息

• Aryl H-phosphonates. Part 11. Synthetic and 31P NMR studies on the formation of aryl nucleoside H-phosphonates †
  作者：Jacek Cieslak、Marzena Szymczak、Malgorzata Wenska、Jacek Stawinski、Adam Kraszewski

  DOI：10.1039/a907150d

  日期：——

  The formation of aryl H-phosphonate diesters from the corresponding nucleoside 3′-H-phosphonates and various phenols was investigated in detail using 31P NMR spectroscopy. The major reaction pathways of aryl nucleoside H-phosphonates under different experimental conditions have been identified and a general method for a clean and efficient generation of these valuable synthetic intermediates was developed

  使用31 P NMR光谱详细研究了由相应的核苷3'-H-膦酸酯和各种酚形成的芳基H-膦酸酯二酯。已经确定了芳基核苷H-膦酸酯在不同实验条件下的主要反应途径，并开发了一种清洁有效地生成这些有价值的合成中间体的通用方法。
• Aryl <i>H-</i>Phosphonates. 12. Synthetic and ³¹P NMR Studies on the Preparation of Nucleoside <i>H-</i>Phosphonothioate and Nucleoside <i>H-</i>Phosphonodithioate Monoesters
  作者：Jacek Cieślak、Jadwiga Jankowska、Jacek Stawiński、Adam Kraszewski

  DOI：10.1021/jo000729q

  日期：2000.10.1

  Transformation of nucleoside H-phosphonate monoesters into the corresponding H-phosphonothioate and H-phosphonodithioate derivatives and possible side-reactions that may accompany this process were studied using (31)P NMR spectroscopy. These provided new insight into a possible mechanism involved in this transformation and constituted the basis for development of efficient methods for the preparation of nucleoside

  使用（31）P NMR光谱研究了将核苷H-膦酸酯单酯转化为相应的H-膦酰硫代酸酯和H-膦酰二硫代酸酯衍生物以及该过程可能伴随的副反应。这些提供了对该转化涉及的可能机理的新见解，并构成了开发有效方法的基础，该方法使用容易获得的H-膦酸酯单酯作为原料制备核苷H-膦酰硫代酸酯和核苷H-膦酰二硫代酸酯单酯。
• Cieslak; Jankowska; Sobkowski, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 1, p. 31 - 37
  作者：Cieslak、Jankowska、Sobkowski、Wenska、Stawinskia、Kraszewski

  DOI：——

  日期：——
• ³¹P NMR Studies on Oxidative Transformations of Aryl Nucleoside H-Phosphonate Diesters
  作者：Annika Kers、Inger Kers、Jacek Cieslak、Adam Kraszewski、Jacek Stawinski

  DOI：10.1080/15257779908041625

  日期：1999.4

  Various aspects of oxidative coupling of nucleoside aryl H-phosphonate diesters with nucleosides to produce important synthetic intermediates in the phosphotriester approach to oligonucleotide synthesis, dinucleoside aryl phosphotriesters, was investigated.
• Use of ammonium aryl H-phosphonates in the preparation of nucleoside H-phosphonate building blocks
  作者：Vita Ozola、Colin B Reese、Quanlai Song

  DOI：10.1016/0040-4039(96)01993-4

  日期：1996.11

  Ammonium 4-methylphenyl H-phosphonate 4c was used in the conversion of 5′-O-(dimethoxytrityl)-2′-deoxynucleoside derivatives 6 into the corresponding 3′-H-phosphonates 2, which were isolated in a high state of purity and in high yield.

  使用4-甲基苯基H-膦酸铵4c将5'- O-（二甲氧基三苯甲基）-2'-脱氧核苷衍生物6转化为相应的3'- H-膦酸酯2，并以高纯度分离得到。高产。