O6-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]guanine | 917376-77-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: O6-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]guanine
• 英文别名: O⁶-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]guanine
• CAS: 917376-77-3
• 化学式: C₃₀H₄₆N₆O₈Si₂
• 分子量: 674.902
• InChiKey: ZEHJGUICSCGZDO-HYFMXHDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  179.14
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  O6-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]guanine 、 1-methyl-3-[2-(4-nitrophenyl)ethoxycarbonyl]imidazolium chloride 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以94%的产率得到O⁶-[2-(4-nitrophenyl)ethyl]-9-{3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}guanine
  参考文献：
  名称：

  Nucleotides. LXXIV Synthesis of a-D-Arabino-oligonucleotides

  摘要：

  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.

  DOI：

  10.1080/15257770500267113
• 作为产物：
  描述：

  N²,N⁹-diacetyl-O⁶-2-(4-nitrophenyl)ethylguanine 在 吡啶 、 盐酸 、 trimethylsilyl trifluorosulfonate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 78.0h， 生成 O6-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]guanine
  参考文献：
  名称：

  Nucleotides. LXXIV Synthesis of a-D-Arabino-oligonucleotides

  摘要：

  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.

  DOI：

  10.1080/15257770500267113