N-[9-((3S,5S,6R)-5-Hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-isobutyramide | 176786-72-4

• 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: N-[9-((3S,5S,6R)-5-Hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-isobutyramide
• 英文别名: N-[9-[(3S,5S,6R)-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 176786-72-4
• 化学式: C₁₅H₂₁N₅O₅
• 分子量: 351.362
• InChiKey: GOVWSJOCPDANIF-LPEHRKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[9-((3S,5S,6R)-5-Hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-isobutyramide 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-pyran-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  1′, 5′ -Anhydrohexitol Oligonucleotides: Synthesis, Base Pairing and Recognition by Regular Oligodeoxyribonucleotides and Oligoribonucleotides

  摘要：

  AbstractOligonucleotides constructed of 1′, 5′‐anhydrohexitol nucleoside building blocks (hexitol nucleic acids, HNA) are completely stable towards 3′‐exonuclease and form very stable self‐complementary duplexes as well as sequence‐selective stable duplexes with the natural DNA and RNA. Triple‐helix formation has also been observed. These hybridisation characteristics are highly dependent on the base sequence and the experimental conditions. When using a phosphate buffer containing 0.1M NaCl, a homopurine HNA dodecamer gives a δTm of +3.0 °C/ base pair with RNA as complement. These oligomers may therefore be of considerable interest as antisense constructs.

  DOI：

  10.1002/chem.19970030118
• 作为产物：
  描述：

  N-[6-Oxo-9-((4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-6,9-dihydro-1H-purin-2-yl]-isobutyramide 在 溶剂黄146 作用下， 反应 5.0h， 生成 N-[9-((3S,5S,6R)-5-Hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-isobutyramide
  参考文献：
  名称：

  1′, 5′ -Anhydrohexitol Oligonucleotides: Synthesis, Base Pairing and Recognition by Regular Oligodeoxyribonucleotides and Oligoribonucleotides

  摘要：

  AbstractOligonucleotides constructed of 1′, 5′‐anhydrohexitol nucleoside building blocks (hexitol nucleic acids, HNA) are completely stable towards 3′‐exonuclease and form very stable self‐complementary duplexes as well as sequence‐selective stable duplexes with the natural DNA and RNA. Triple‐helix formation has also been observed. These hybridisation characteristics are highly dependent on the base sequence and the experimental conditions. When using a phosphate buffer containing 0.1M NaCl, a homopurine HNA dodecamer gives a δTm of +3.0 °C/ base pair with RNA as complement. These oligomers may therefore be of considerable interest as antisense constructs.

  DOI：

  10.1002/chem.19970030118

文献信息

• Improved Synthesis of Anhydrohexitol Building Blocks for Oligonucleotide Synthesis
  作者：Bart De Bouvere、Luc Kerremans、Jef Rozenski、Gerard Janssen、Arthur van Aerschot、Paul Claes、Roger Busson、Piet Herdewijn

  DOI：10.1002/jlac.199719970724

  日期：1997.7

  The synthesis of the four building blocks used for the preparation of hexitol nucleic acids were optimized. The nucleoside analogues with a purine base moiety are best prepared by a nucleophilic substitution reaction, whereas the pyrimidine nucleosides can best be obtained using Mitsunobu-type conditions.

  优化了用于制备己糖醇核酸的四个构件的合成。具有嘌呤碱基部分的核苷类似物最好通过亲核取代反应制备，而嘧啶核苷可以使用Mitsunobu型条件获得最佳。