2',3',4'-tri-O-benzoyl-β-D-xylopyranosyl thymine | 166830-00-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',3',4'-tri-O-benzoyl-β-D-xylopyranosyl thymine
• 英文别名: 1-(2',3',5'-tri-O-benzoyl-β-D-xylopyranosyl)thymine；[(3R,4S,5R,6R)-4,5-dibenzoyloxy-6-(5-methyl-2,4-dioxopyrimidin-1-yl)oxan-3-yl] benzoate
• CAS: 166830-00-8
• 化学式: C₃₁H₂₆N₂O₉
• 分子量: 570.555
• InChiKey: HKKQBZXXQBJLSJ-SPGPFUFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  42.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  142.99
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2',3',4'-tri-O-benzoyl-β-D-xylopyranosyl thymine 在 palladium on activated charcoal 吡啶 、 4 A molecular sieve 、 氨 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 1-{3'-O-acetyl-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-β-D-xylopyranosyl}thymine
  参考文献：
  名称：

  Pentopyranosyl 寡核苷酸系统，Communication No.12，Theβ-D-Xylopyranosyl-(4'→2'-寡核苷酸系统

  摘要：

  beta-D-Xylopyranosyl-(4'-->2')-oligonucleotides containing adenine and thymine as nucleobases were synthesized as a part of a systematic study of the pairing properties of pentopyranosyl oligonucleotides. Contrary to earlier expectations based on qualitative conformational criteria, beta-D-xylopyranosyl-(4'-->2')oligonucleotides show Watson-Crick pairing comparable in strength to that shown by pyranosyl-RNA.

  DOI：

  10.1002/1522-2675(200202)85:2<399::aid-hlca399>3.0.co;2-2
• 作为产物：
  描述：

  胸腺嘧啶 、 tetrabenzoyl-D-xylopyranose 在 苯磺酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以91%的产率得到2',3',4'-tri-O-benzoyl-β-D-xylopyranosyl thymine
  参考文献：
  名称：

  Pentopyranosyl 寡核苷酸系统，Communication No.12，Theβ-D-Xylopyranosyl-(4'→2'-寡核苷酸系统

  摘要：

  beta-D-Xylopyranosyl-(4'-->2')-oligonucleotides containing adenine and thymine as nucleobases were synthesized as a part of a systematic study of the pairing properties of pentopyranosyl oligonucleotides. Contrary to earlier expectations based on qualitative conformational criteria, beta-D-xylopyranosyl-(4'-->2')oligonucleotides show Watson-Crick pairing comparable in strength to that shown by pyranosyl-RNA.

  DOI：

  10.1002/1522-2675(200202)85:2<399::aid-hlca399>3.0.co;2-2

文献信息

• 3′-Deoxy-3′-hydroxymethyl-aldopentopyranosyl nucleoside synthesis. Part I
  作者：Bogdan Doboszewski、Norbert Blaton、Jef Rozenski、André De Bruyn、Piet Herdewijn

  DOI：10.1016/0040-4020(95)00211-p

  日期：1995.5

  A straightforward synthesis of 3′-deoxy-3′-hydroxymethyl-aldopentopyranosyl nucleosides is described starting from β-d-xylopyranosyl nucleosides. β-d-xylopyranosyl thymine 17a,b,c and uracil 17d are converted into the 4′-benzoylated derivatives 18a,b and further into the 2′,3′-enepyranosyl compounds 19b,c. A 3′-hydroxymethyl appendix has been introduced using a free-radical methodology to furnish 20a

  从β-d-吡喃吡喃糖基核苷开始描述了3'-脱氧-3'-羟甲基-醛基戊吡喃糖基核苷的直接合成。将β-d-吡喃喃喃糖基胸腺嘧啶17a，b，c和尿嘧啶17d转化为4′-苯甲酰化衍生物18a，b，并进一步转化为2′，3′-烯吡喃糖基化合物19b，c。已经使用自由基方法引入了3'-羟甲基附录来提供20a，b。反转4'-位置的构型产生靶核苷22a，b。X射线和1 H NMR构象分析证明了目标化合物中碱基部分的赤道取向。