1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[ethenyl(methoxy)phosphoryl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione | 364063-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[ethenyl(methoxy)phosphoryl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 364063-63-8
• 化学式: C₁₉H₃₃N₂O₇PSi
• 分子量: 460.539
• InChiKey: LFGXTIVFLBTLDX-QUIPRKFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[ethenyl(methoxy)phosphoryl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione 、 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 ((Z)-Styryl)-phosphonic acid (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester methyl ester 、 ((E)-Styryl)-phosphonic acid (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester methyl ester
  参考文献：
  名称：

  An Olefin Cross-Metathesis Approach to Vinylphosphonate-Linked Nucleic Acids

  摘要：

  [GRAPHICS]The synthesis of vinylphosphonate-linked nucleotide dimers has been achieved using an olefin cross-metathesis (CM) reaction as a key step. The 1,3-dimesityl-4,5-dihydroimidazol-2-ylidine-containing catalyst 5 (Grubbs' second-generation catalyst) was found to be the superior catalyst for this transformation. Both metathesis partners were readily available using known methodology, and the vinylphosphonate-linked dimer was produced with high levels of (E)-selectivity (> 20:1) in 58% yield (70% based on recovered starting material).

  DOI：

  10.1021/ol016366d
• 作为产物：
  描述：

  溴乙烯 、 1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[methoxy(oxido)phosphaniumyl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 palladium diacetate 、 三苯基膦 、 methyloxirane 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以64%的产率得到1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[ethenyl(methoxy)phosphoryl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  An Olefin Cross-Metathesis Approach to Vinylphosphonate-Linked Nucleic Acids

  摘要：

  [GRAPHICS]The synthesis of vinylphosphonate-linked nucleotide dimers has been achieved using an olefin cross-metathesis (CM) reaction as a key step. The 1,3-dimesityl-4,5-dihydroimidazol-2-ylidine-containing catalyst 5 (Grubbs' second-generation catalyst) was found to be the superior catalyst for this transformation. Both metathesis partners were readily available using known methodology, and the vinylphosphonate-linked dimer was produced with high levels of (E)-selectivity (> 20:1) in 58% yield (70% based on recovered starting material).

  DOI：

  10.1021/ol016366d

文献信息

• An Olefin Cross-Metathesis Approach to Vinylphosphonate-Linked Nucleic Acids
  作者：Manuel Lera、Christopher J. Hayes

  DOI：10.1021/ol016366d

  日期：2001.8.1

  [GRAPHICS]The synthesis of vinylphosphonate-linked nucleotide dimers has been achieved using an olefin cross-metathesis (CM) reaction as a key step. The 1,3-dimesityl-4,5-dihydroimidazol-2-ylidine-containing catalyst 5 (Grubbs' second-generation catalyst) was found to be the superior catalyst for this transformation. Both metathesis partners were readily available using known methodology, and the vinylphosphonate-linked dimer was produced with high levels of (E)-selectivity (> 20:1) in 58% yield (70% based on recovered starting material).