1-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)thymine | 127761-89-1

• 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: 1-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)thymine
• 英文别名: [(2R,3R,4S,5S)-3,4-diacetyloxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 127761-89-1
• 化学式: C₁₆H₂₀N₂O₉
• 分子量: 384.343
• InChiKey: XMDWATDROXTTHT-CXTNEJHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  142.99
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  胸腺嘧啶 在 硫酸氢铵 、 trimethylsilyl trifluorosulfonate 作用下， 以 甲苯 为溶剂， 反应 21.0h， 生成 1-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)thymine
  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

文献信息

• Stereospecific Vorbrueggen-like reactions of 1,2-anhydro sugars. An alternative route to the synthesis of nucleosides
  作者：Ken Chow、Samuel Danishefsky

  DOI：10.1021/jo00300a049

  日期：1990.6
• CHOW, KEN;DANISHEFSKY, SAMUEL, J. ORG. CHEM., 55,(1990) N3, C. 4211-4214
  作者：CHOW, KEN、DANISHEFSKY, SAMUEL

  DOI：——

  日期：——