5-甲基-N-(三甲基甲硅烷基)-2-[(三甲基甲硅烷基)氧基]-4-嘧啶胺 | 32865-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-甲基-N-(三甲基甲硅烷基)-2-[(三甲基甲硅烷基)氧基]-4-嘧啶胺
• 英文名称: 2'-O,N⁴-bis-trimethylsilyl-5-methylcytosine
• 英文别名: disilyl-5-methylcytosine；(5-methyl-2-trimethylsilanyloxy-pyrimidin-4-yl)-trimethylsilanyl-amine；5-Methylcytosin-O²,N⁴-bis (trimethylsilyl)；O²,N⁴-Bistrimethylsilyl-5-methylcytosin；4-Pyrimidinamine, 5-methyl-N-(trimethylsilyl)-2-[(trimethylsilyl)oxy]-；5-methyl-N-trimethylsilyl-2-trimethylsilyloxypyrimidin-4-amine
• CAS: 32865-88-6
• 化学式: C₁₁H₂₃N₃OSi₂
• 分子量: 269.494
• InChiKey: MMERKIUBCROXJL-UHFFFAOYSA-N

物化性质

• 保留指数：
  1546;1544;1533;1533;1537;1537;1537;1538;1533;1536.3;1556.8

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-甲基-N-(三甲基甲硅烷基)-2-[(三甲基甲硅烷基)氧基]-4-嘧啶胺 在 吡啶 、 N-甲基咪唑 、 2,3,5-三甲基吡啶 、 sodium hydroxide 、 sodium methylate 、 silver nitrate 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 N-[1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-5-methyl-2-oxopyrimidin-4-yl]benzamide
  参考文献：
  名称：

  Recognition of RNA by triplex formation: Divergent effects of pyrimidine C-5 methylation

  摘要：

  In DNA triple helices, methylation at C-5 of thymine or cytosine is reported to have similar stabilizing effects for both bases. Here we show, however, that methylation of the same positions in RNA triplexes has distinctly different effects than in DNA. We have previously described the use of circular tripler-forming RNA oligonucleotides to recognize RNA sequences. Here it is shown that addition of C-5 methyl groups to uracils in these compounds very significantly increases not only affinity but also sequence selectivity in binding a purine-rich RNA target, as measured by thermal denaturation with various target RNAs. Surprisingly, however, addition of C-5 methyl groups to cytosines actually decreases affinity in binding RNA, while the same substitution in DNA is thermally stabilizing. possible sources of this divergent behavior are discussed. A synthesis of 5-methylcytidine ribonucleoside 2'-O-silyl-3'-O-phosphoramidite is also described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00059-x
• 作为产物：
  描述：

  5-甲基胞嘧啶 、 六甲基二硅氮烷 反应 5.0h， 生成 5-甲基-N-(三甲基甲硅烷基)-2-[(三甲基甲硅烷基)氧基]-4-嘧啶胺
  参考文献：
  名称：

  Recognition of RNA by triplex formation: Divergent effects of pyrimidine C-5 methylation

  摘要：

  In DNA triple helices, methylation at C-5 of thymine or cytosine is reported to have similar stabilizing effects for both bases. Here we show, however, that methylation of the same positions in RNA triplexes has distinctly different effects than in DNA. We have previously described the use of circular tripler-forming RNA oligonucleotides to recognize RNA sequences. Here it is shown that addition of C-5 methyl groups to uracils in these compounds very significantly increases not only affinity but also sequence selectivity in binding a purine-rich RNA target, as measured by thermal denaturation with various target RNAs. Surprisingly, however, addition of C-5 methyl groups to cytosines actually decreases affinity in binding RNA, while the same substitution in DNA is thermally stabilizing. possible sources of this divergent behavior are discussed. A synthesis of 5-methylcytidine ribonucleoside 2'-O-silyl-3'-O-phosphoramidite is also described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00059-x
• 作为试剂：
  描述：

  1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose 、 5-甲基-N-(三甲基甲硅烷基)-2-[(三甲基甲硅烷基)氧基]-4-嘧啶胺 在 5-甲基-N-(三甲基甲硅烷基)-2-[(三甲基甲硅烷基)氧基]-4-嘧啶胺 作用下， 生成
  参考文献：
  名称：

  MODULAR RADIOCHEMISTRY SYNTHESIS SYSTEM

  摘要：

  一种模块化化学生产系统包括多个模块，用于在远程位置执行化学反应，特别是放射性化合物的反应。其中一种实施方式包括反应容器，包括可移动的热源，其相对于反应容器的位置可从远程位置控制。或者，热源可以固定在位置上，反应瓶可移动进入和移出热源。反应容器具有一个或多个密封塞，其相对于反应容器的位置可从远程位置控制。此外，一个或多个反应容器密封塞可以包括一个或多个管道，用于输送反应物、大气或升高压力下的气体、惰性气体、抽真空和将反应终产物从反应瓶中移除，密封塞位置可在升高压力下操作反应瓶。该模块化化学生产系统由模块组装而成，每个模块可以包括操作条件传感器和控制器，用于从远程位置监视和控制各个模块和组装系统。其他模块包括但不限于试剂储存和输送模块、柱层纯化模块、微波反应模块、外部QC/分析/纯化接口模块、分样模块、F-18干燥模块、浓缩模块、辐射计数模块和毛细管反应器模块。

  公开号：

  US20150329583A1

文献信息

• Nucleotides. LXXIV Synthesis of a-D-Arabino-oligonucleotides
  作者：Christoph Henke、Wolfgang Pfleiderer

  DOI：10.1080/15257770500267113

  日期：2005.9.1

  The 5 alpha-D-arabinofuranosylnucleosides alpha-araU (15), alpha-araT (18), alpha-araC (22), alpha-araA (25), and alpha-araG (28) have been synthesized by the modified silyl-method. The amino groups at the nucleobases and the 2'-hydroxy group at the sugar moiety were protected by the 2-(4-nitro-phenyl) ethoxycarbonyl (npeoc) group (37-40) and the amide function in alpha-araG was additionally blocked by the 2-(4-nitrophenyl)ethyl group (63) to improve solubility in organic solvents. Mono-and dimethoxytritylation of the 5'-OH group was performed in the usual manner to give 41-48, 64, and 65 in high yields and further substitution of the 3'-OH group led to the monomeric building blocks 66-75 as well as the 3'-O-succinoyl derivatives 76-85 functioning as starting units in solid-support oligonucleotide synthesis. A large number of oligo-alpha-arabinonucleotides have been prepared on modified CPG-material applying the npeoc/npe strategy as a very efficient synthetic tool for highly purified, homogenous oligomers. Hybridizations between alpha-arabinonucleotide strands revealed in analogy to earlier findings an antiparallel orientation whereas the combination of an oligo-alpha-D-arabinonucleotide with a complementary oligo-2'-deoxy-beta-D-ribofuranosylnucleotide showed base-pairing only if a parallel polarity was present. The advantages in oligo-alpha-arabinonucleotide synthesis were furthermore demonstrated by the synthesis of the t alpha-ANA(his) a structural analog of the natural tRNA(his) of the phage T5.

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