2-(2(R)-(tert-butyldimethylsilyl)oxymethyl-5(R)-(thymin-1-yl)tetrahydrofuran-3(S)-oxyl)-2-oxo-4,7-dihydro-1,3-dioxa-2-phosphepine | 321130-16-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 2-(2(R)-(tert-butyldimethylsilyl)oxymethyl-5(R)-(thymin-1-yl)tetrahydrofuran-3(S)-oxyl)-2-oxo-4,7-dihydro-1,3-dioxa-2-phosphepine
• CAS: 321130-16-9
• 化学式: C₂₀H₃₃N₂O₈PSi
• 分子量: 488.55
• InChiKey: KSPAEMNXRAXCMP-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  118.08
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-(2(R)-(tert-butyldimethylsilyl)oxymethyl-5(R)-(thymin-1-yl)tetrahydrofuran-3(S)-oxyl)-2-oxo-4,7-dihydro-1,3-dioxa-2-phosphepine 在 三氟乙酸 作用下， 反应 0.25h， 以93%的产率得到2-(2(R)-hydroxymethyl-5(R)-(thymin-1-yl)tetrahydrofuran-3(S)-oxyl)-2-oxo-4,7-dihydro-1,3-dioxa-2-phosphepine
  参考文献：
  名称：

  Synthesis of Conformationally Restricted Dinucleotides by Ring-Closing Metathesis

  摘要：

  [GRAPHICS]The ring closing metathesis reaction has been used in the synthesis of conformationally restricted dinucleotides as well as a 3'-nucleotide analogue. From bis-allylic nucleoside phosphates obtained from simple nucleoside precursors, the synthesis of unsaturated cyclophosphates has been accomplished using either Grubbs' catalyst or an improved analogue. Hereby, the conformational freedom of the nucleic acid phosphordiester linkage has been efficiently constrained.

  DOI：

  10.1021/ol0067639
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 四氮唑 、 叔丁基过氧化氢 、 二异丙胺 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 19.25h， 生成 2-(2(R)-(tert-butyldimethylsilyl)oxymethyl-5(R)-(thymin-1-yl)tetrahydrofuran-3(S)-oxyl)-2-oxo-4,7-dihydro-1,3-dioxa-2-phosphepine
  参考文献：
  名称：

  Synthesis of Conformationally Restricted Dinucleotides by Ring-Closing Metathesis

  摘要：

  [GRAPHICS]The ring closing metathesis reaction has been used in the synthesis of conformationally restricted dinucleotides as well as a 3'-nucleotide analogue. From bis-allylic nucleoside phosphates obtained from simple nucleoside precursors, the synthesis of unsaturated cyclophosphates has been accomplished using either Grubbs' catalyst or an improved analogue. Hereby, the conformational freedom of the nucleic acid phosphordiester linkage has been efficiently constrained.

  DOI：

  10.1021/ol0067639