Carbonic acid (2R,3S,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-(2-nitro-phenyl)-propyl ester | 339571-01-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: Carbonic acid (2R,3S,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-(2-nitro-phenyl)-propyl ester
• CAS: 339571-01-6
• 化学式: C₃₆H₄₁N₃O₉Si
• 分子量: 687.822
• InChiKey: ZACXOFKTOZTJOH-LZYNLJSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  49.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  151.99
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Carbonic acid (2R,3S,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-(2-nitro-phenyl)-propyl ester 在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine
  参考文献：
  名称：

  3‘-Nitrophenylpropyloxycarbonyl (NPPOC) Protecting Groups for High-Fidelity Automated 5‘ → 3‘ Photochemical DNA Synthesis

  摘要：

  The most powerful DNA microarrays would be prepared by photolithography with free 3'-ends that could be processed enzymatically, A photoremovable group that could be removed in quantitative yield would ensure high purity of the synthesized probes. We have developed new pyrimidine building blocks for 5' - 3' DNA synthesis with high cycle yields using the NPPOC (3' nitrophenylpropyloxycarbonyl) protecting group. These phosphoramidites were proved in automated photochemical DNA synthesis on a modified synthesizer.

  DOI：

  10.1021/ol0069150
• 作为产物：
  描述：

  beta-甲基-2-硝基-苯乙醇 在 吡啶 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 14.0h， 生成 Carbonic acid (2R,3S,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-(2-nitro-phenyl)-propyl ester
  参考文献：
  名称：

  3‘-Nitrophenylpropyloxycarbonyl (NPPOC) Protecting Groups for High-Fidelity Automated 5‘ → 3‘ Photochemical DNA Synthesis

  摘要：

  The most powerful DNA microarrays would be prepared by photolithography with free 3'-ends that could be processed enzymatically, A photoremovable group that could be removed in quantitative yield would ensure high purity of the synthesized probes. We have developed new pyrimidine building blocks for 5' - 3' DNA synthesis with high cycle yields using the NPPOC (3' nitrophenylpropyloxycarbonyl) protecting group. These phosphoramidites were proved in automated photochemical DNA synthesis on a modified synthesizer.

  DOI：

  10.1021/ol0069150