1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-bis(phenylsulfanyl)phosphoryloxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione | 80585-43-9

• 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)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-bis(phenylsulfanyl)phosphoryloxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 80585-43-9
• 化学式: C₄₃H₄₁N₂O₈PS₂
• 分子量: 808.913
• InChiKey: ZMGKOASQPHAXBN-KQIHHXPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  56
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  163
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-bis(phenylsulfanyl)phosphoryloxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 次磷酸 、 N,N-二异丙基乙胺 作用下， 以 吡啶 为溶剂， 反应 15.25h， 生成 triethylammonium S-phenyl 5'-O-(4,4'-dimethoxytrityl)-3-N-benzoylthymidine 3'-phosphorothioate
  参考文献：
  名称：

  磷酸三酯法中用于快速形成核苷酸间键的新型缩合试剂以及制备n 3-苯甲酰胸苷作为寡聚脱氧核糖核苷酸合成的关键中间体的方法

  摘要：

  在磷酸三酯方法快速间键形成已通过使用双（2,4,6-三trihalophenyl）phosphorochloridates（TCP和TBP）作为新的冷凝试剂和苯甲酰基作为N的以高产率取得3的亚胺保护基团胸腺嘧啶核苷。

  DOI：

  10.1016/0040-4039(84)80055-6
• 作为产物：
  描述：

  cyclohexylammonium S,S-diphenyl phosphorodithioate 、 保护胸苷 在 氨苯砜 作用下， 以 吡啶 为溶剂， 反应 4.0h， 以98%的产率得到1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-bis(phenylsulfanyl)phosphoryloxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  自互补四脱氧核糖核苷三磷酸在溶液中的便捷化学制备和光谱研究

  摘要：

  通过简化的方法制备了八种自互补的四脱氧核糖核苷三磷酸酯，这使我们能够省略合成中间体的纯化，并提供了非常快速和方便的四聚体。通过酶测定法表征四聚体，并通过在各种条件下使用UV和CD光谱法研究它们的构象。CD光谱的详细分析表明，四聚体双链体的构象取决于序列。

  DOI：

  10.1016/s0040-4020(01)87448-2

文献信息

• Oligodeoxyribonucleotide synthesis by use of S,S-diphenyl deoxyribonucleoside 3'-phosphorodithioates and bifunctional condensing reagents in the phosphotriester approach
  作者：Mitsuo Sekine、Jun-Ichi Matsuzaki、Tsujiaki hata

  DOI：10.1016/s0040-4020(01)96778-x

  日期：1985.1

  This paper describes detailed studies on the selective removal of one of two phenylthio groups by means of phosphinates from S,S-diphenyl deoxyribonucleoside 3'-phosphorodithioate derivatives, which were successfully used as the starting building units for the liquid phase synthesis of a dodecadeoxyribonucleotide, dCATTATTAATAC.

  合成了四种芳香二磺酰氯作为寡聚脱氧核糖核苷酸合成的缩合剂，并在胸苷基（3'-5'）胸腺嘧啶核苷的合成中考察了它们的缩合能力。其中，均三甲苯二磺酰氯（MDS）和异二烯丙基异磺酰氯（DDS）被证明对于缩合和从同时形成的5'-磺化副产物中分离产物是有效的。本文详细描述了通过次膦酸酯从S，S-二苯基脱氧核糖核苷3'-磷酸二硫酯衍生物中选择性除去两个苯硫基之一的研究，这些衍生物已成功地用作液相合成十二烷氧基核糖核苷酸的起始结构单元， dCATTATTAATAC。
• Phosphotriester approach to oligothymidylate synthesis utilizing a simple thymidine unit and a new type of condensing agents
  作者：Mitsuo Sekine、Jun-ichi Matsuzaki、Tsujiaki Hata

  DOI：10.1016/s0040-4039(01)81865-7

  日期：1981.1
• Biologically Active Oligodeoxyribonucleotides. 5. 5‘-End-Substituted d(TGGGAG) Possesses Anti-Human Immunodeficiency Virus Type 1 Activity by Forming a G-Quadruplex Structure
  作者：Hitoshi Hotoda、Makoto Koizumi、Rika Koga、Masakatsu Kaneko、Kenji Momota、Toshinori Ohmine、Hidehiko Furukawa、Toshinori Agatsuma、Takashi Nishigaki、Junko Sone、Shinya Tsutsumi、Toshiyuki Kosaka、Koji Abe、Satoshi Kimura、Kaoru Shimada

  DOI：10.1021/jm970658w

  日期：1998.9.1

  A series of hexadeoxyribonucleotides (6-mers), d(TGGGAG), substituted with a variety of aromatic groups at the 5'-end were synthesized and tested for anti-human immunodeficiency virus type 1 (HIV-1) activity. While unmodified d(TGGGAG) (31) had no anti-HIV-l activity, compound 23 with a 3,4-di(benzyloxy)benzyl (DBB) group at the 5'-end potently inhibited the HIV-1(IIIB)-induced cytopathicity of MT-4 cells in vitro (IC50 = 0.37 mu M) without cytotoxicity up to 40 mu M. A thermal denaturation study on the 5'-end-substituted 6-mers by means of the circular dichroism (CD) spectra demonstrated that the aromatic substituent attached at the 5'-end of the 6-mer strongly enhanced the formation of a parallel helical structure consisting of four strands (quadruplex). On the contrary, compound 36, in which one of the guanosines of 23 was replaced by a thymidine, did not form a quadruplex, thus exhibiting no anti-HIV-1 activity. Moreover, both compound 15, with a tert-butyldiphenylsilyl group solely at its 3'-end, and compound 21, with a relatively small substituent, a benzyl group, at the 5'-end, formed quadruplexes but had no anti-HIV-1 activity. These findings led us to the conclusion that both the quadruplex structure and the aromatic substituent with adequate size at the 5'-end are crucial for the interaction of the 5'-end-substituted 6-mers with the V3 loop as well as the CD4 binding site on viral gp120, resulting in anti-HIV-1 activity.
• MATSUZAKI, JUN-ICHI;HOTODA, HITOSHI;SEKINE, MITSUO;HATA, TSUJIAKI, 12TH SYMP. NUCL. ACIDS CHEM., KANAZAWA, OCT. 30 - NOV. 1, 1984, OXFORD; W+
  作者：MATSUZAKI, JUN-ICHI、HOTODA, HITOSHI、SEKINE, MITSUO、HATA, TSUJIAKI

  DOI：——

  日期：——
• XATA, TSUDZIAKI;SEHKINEH, MITSUO;MATSUDZAKI, DZYUNITI;XOTODO, MASASI
  作者：XATA, TSUDZIAKI、SEHKINEH, MITSUO、MATSUDZAKI, DZYUNITI、XOTODO, MASASI

  DOI：——

  日期：——