1-(β-D-xylopyranosyl)thymine | 114612-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(β-D-xylopyranosyl)thymine
• 英文别名: 5-methyl-1-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]pyrimidine-2,4-dione
• CAS: 114612-02-1
• 化学式: C₁₀H₁₄N₂O₆
• 分子量: 258.231
• InChiKey: HBXOULCXYFWEKF-JVZYCSMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(β-D-xylopyranosyl)thymine 在 palladium on activated charcoal 吡啶 、 4 A molecular sieve 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 吡啶 、 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：

  tetrabenzoyl-D-xylopyranose 在 苯磺酰胺 、 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 生成 1-(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。
• The Use of Phosphorous Acid Chlorides in Peptide Synthesis¹
  作者：Richard W. Young、Kathryn H. Wood、R. Janice Joyce、George W. Anderson

  DOI：10.1021/ja01591a026

  日期：1956.5
• Phosphonates Derivatives of 2',3'-Dideoxy-2',3'-didehydro-pentopyranosyl Nucleosides
  作者：María-Jesús Péarez-Péarez、Bogdan Doboszewski、Erik De Clercq、P. Herdewijn

  DOI：10.1080/15257779508012454

  日期：1995.5.1
• The Synthesis of Nucleosides of Cytosine and 5-Methylcytosine¹
  作者：Jack J. Fox、Irving Goodman

  DOI：10.1021/ja01151a076

  日期：1951.7
• Pentopyranosyl Oligonucleotide Systems, Communication No.12, Theβ-D-Xylopyranosyl-(4′→2′-oligonucleotide System
  作者：Thomas Wagner、Hoan K. Huynh、Ramanarayanan Krishnamurthy、Albert Eschenmoser

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

  日期：2002.2

  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.