(S_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate | 133574-79-5

• 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: (S_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate
• 英文别名: (Sp)-N⁶-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<(1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate；(S_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N⁶-benzoyl-3'-O-[1,1-dimethylethyl)dimethylsilyl]-2'-deoxyadenosine 3'-methylphosphonate
• CAS: 133574-79-5
• 化学式: C₆₂H₆₇N₁₀O₁₁PSi
• 分子量: 1187.33
• InChiKey: OCYZNFLAPOZMJN-QRRHGOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.39
• 重原子数：
  85.0
• 可旋转键数：
  21.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  236.31
• 氢给体数：
  2.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  (S_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 (S)-Methyl-phosphonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Diastereomerically pure Rp and Sp dinucleoside H-phosphonates: the stereochemical course of their conversion into P-methylphosphonates, phosphorothioates, and [oxygen-18] chiral phosphates

  摘要：

  DOI：

  10.1021/jo00012a017
• 作为产物：
  描述：

  N-苯甲酰-2'-脱氧-3'-O-(1,1-二甲基乙基)二甲基硅氧基-腺苷 在 吡啶 、 正丁基锂 、 三甲基乙酰氯 作用下， 反应 0.75h， 生成 (S_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate
  参考文献：
  名称：

  Diastereomerically pure Rp and Sp dinucleoside H-phosphonates: the stereochemical course of their conversion into P-methylphosphonates, phosphorothioates, and [oxygen-18] chiral phosphates

  摘要：

  DOI：

  10.1021/jo00012a017

文献信息

• Enantiodivergent Formation of C–P Bonds: Synthesis of P-Chiral Phosphines and Methylphosphonate Oligonucleotides
  作者：Dongmin Xu、Nazaret Rivas-Bascón、Natalia M. Padial、Kyle W. Knouse、Bin Zheng、Julien C. Vantourout、Michael A. Schmidt、Martin D. Eastgate、Phil S. Baran

  DOI：10.1021/jacs.9b13898

  日期：2020.3.25

  Phosphorous Incorporation (PI, abbreviated Π) reagents for the modular, scalable, and stereospecific synthesis of chiral phosphines and methyl-phosphonate nucleotides are reported. Synthesized from trans-limonene oxide, this reagent class displays an unexpected reactivity profile and enables access to chemical space distinct from that of the Phosphorous-Sulfur Incorporation reagents previously disclosed

  报告了用于手性膦和甲基膦酸核苷酸的模块化、可扩展和立体特异性合成的磷结合 (PI，缩写为 Π) 试剂。该试剂类由反式柠檬烯氧化物合成，显示出意想不到的反应性特征，并能够进入与之前公开的磷硫结合试剂不同的化学空间。在这里，适应性强的磷 (V) 支架能够连续添加碳亲核试剂以产生各种对映纯 CP 构建块。将三个碳亲核试剂添加到 Π，然后进行立体有择还原，得到有用的 P-手性膦；引入而不是单个甲基揭示了甲基膦酸酯寡核苷酸前体的首次立体定向合成。虽然两种 Π 对映异构体都可用，
• Phosphoramidites of (Rp) and (Sp)-Configurated Adenosine Methylphosphonate Dimers
  作者：Markus Schweitzer、Wendelin Samstag、Joachim Engels

  DOI：10.1080/15257779508012479

  日期：1995.5.1

  The synthesis of adenosine methylphosphonate dimers, the separation of the diastereomers and the conversion into phosphoramidites is presented. These dimer building blocks were tested in the solid phase DNA synthesis of the hairpin decanucleotide 5'-CGCAAAAGCG-3'.