1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(phenylmethoxyamino)methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione | 291753-12-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(phenylmethoxyamino)methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 291753-12-3
• 化学式: C₂₃H₃₅N₃O₅Si
• 分子量: 461.634
• InChiKey: DIUHAYQPRCMFDW-XUVXKRRUSA-N

物化性质

• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  89.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(phenylmethoxyamino)methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 O-(1H-benzotriazol-1-yl)-N,N,N'N'-tetramethyluronium BF₆^(1-) 、 四丁基氟化铵 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2-[(2S,3R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N-[[(2R,3S,5R)-3-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]-N-phenylmethoxyacetamide
  参考文献：
  名称：

  含有异羟肟酸酯键的寡核苷酸的合成和生物物理研究。

  摘要：

  合成了含有异羟肟酸酯键的新型胸苷二聚体，将其掺入寡核苷酸序列并研究了它们对互补DNA和RNA靶标的杂交特性。

  DOI：

  10.1081/ncn-100002513
• 作为产物：
  描述：

  3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde 在 吡啶 、 sodium cyanoborohydride 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 18.0h， 生成 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(phenylmethoxyamino)methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  含有异羟肟酸酯键的寡核苷酸的合成和生物物理研究。

  摘要：

  合成了含有异羟肟酸酯键的新型胸苷二聚体，将其掺入寡核苷酸序列并研究了它们对互补DNA和RNA靶标的杂交特性。

  DOI：

  10.1081/ncn-100002513

文献信息

• Synthesis and biophysical studies of oligonucleotides containing hydroxamate linkages
  作者：Kanda S Ramasamy、Liyan He、Vesna Stoisavljevic、Brent Harpham、Wilfried Seifert

  DOI：10.1016/s0040-4039(00)00661-4

  日期：2000.6

  Novel oligonucleotide dimers containing hydroxamate linkages (15 and 16) were synthesized, incorporated into oligonucleotide sequences and studied for their hybridization properties with complementary DNA and RNA targets. The modified oligonucleotides showed similar binding properties and enhanced resistance to exonucleases compared to natural oligonucleotides.

  合成了包含异羟肟酸酯键（15和16）的新型寡核苷酸二聚体，将其掺入寡核苷酸序列中，并研究了它们与互补DNA和RNA靶标的杂交特性。与天然寡核苷酸相比，修饰的寡核苷酸显示出相似的结合特性并增强了对核酸外切酶的抗性。
• Syntheses and binding studies of oligonucleotides containing N-hydroxycarbamate linkages: potential DNA cleaving antisense oligomers
  作者：Hui Li、Marvin J Miller

  DOI：10.1016/s0040-4039(00)00662-6

  日期：2000.6

  An efficient synthesis of N-hydroxycarbamate containing thymidine dimer 9 was accomplished and it was incorporated into automatic DNA syntheses to make thymidine 16mers T*-1, T*-2 and T*-3. Binding abilities of T*-1, T*-2 and T*-3 with poly (dA)-16mer were assayed by melting denaturation (Tm) studies of the corresponding duplexes. Iron binding ability of a thymidine oligomer with N-hydroxycarbamate linkages was studied by MALDI-MS. Nuclease stability assays showed that the modified oligonucleotides have enhanced resistance toward nuclease SI (endonuclease) compared to natural oligonucleotides. (C) 2000 Elsevier Science Ltd. All rights reserved.