1'-homo-N-α-thymidine | 175672-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1'-homo-N-α-thymidine
• 英文别名: 1-[[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl]-5-methylpyrimidine-2,4-dione
• CAS: 175672-64-7
• 化学式: C₁₁H₁₆N₂O₅
• 分子量: 256.258
• InChiKey: MRYRQQBKWQZCCY-XHNCKOQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1'-homo-N-α-thymidine 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 1.0h， 生成 1-[[(2S,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]methyl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of (2-Deoxy-α- and -β-d-erythro-pentofuranosyl)(thymin-1-yl)alkanes and Their Incorporation into Oligodeoxyribonucleotides. Effect of Nucleobase−Sugar Linker Flexibility on the Formation of DNA−DNA and DNA−RNA Hybrids

  摘要：

  On the basis of modeling studies, the (2-deoxy-alpha- and beta-D-erythro-pentofuranosyl) (thymin-1-yl) alkanes 1a,b and 2a,b were selected as potential conformational probes for altDNA oligonucleotides. A straightforward approach to the synthesis of 1a,b and 2a,b from commercial 2-deoxy-D-ribose (3) and 1-O-methyl-2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentofuranose (13), respectively, was developed. These nucleoside analogues were converted to the phosphoramidite derivatives 27a,b-30a,b and incorporated into oligonucleotide 31 at predetermined sites and defined internucleotidic motifs. The insertion of 1a,b according to either a (3' --> 5')- or a (3' --> 3')-internucleotidic polarity produced oligonucleotides exhibiting a slightly higher affinity for their complementary unmodified DNA sequence than for the corresponding RNA sequence (Table 3). Conversely, the incorporation of 2a into 31 according to a (3' --> 3')-orientation generated, for the first time, an altDNA oligonucleotide displaying a greater affinity for its complementary unmodified RNA sequence (Delta T-m = 6 degrees C) than for the corresponding DNA sequence (Delta T-m = 10 degrees C). thermodynamically less stable than the duplex having unmodified alpha-2'-deoxythymidine similarly incorporated into 31 (Delta Delta T-m = 3 degrees C).

  DOI：

  10.1021/jo961548k
• 作为产物：
  描述：

  2-deoxy-3,5-di-O-p-toluoyl-α-D-erythropentofuranosyl 1-cyanide 在 盐酸 、 甲醇 、 氢氧化钾 、 硼烷 、 三乙胺 作用下， 以 乙醇 、 水 、 溶剂黄146 、 苯 为溶剂， 反应 33.17h， 生成 1'-homo-N-α-thymidine
  参考文献：
  名称：

  [(2-Deoxy-α- and β-D-erythro-pentofuranosyl)thymin-1-YL] methane derivatives as potential conformational probes for altDNA oligonucleotides

  摘要：

  The previously unknown deoxyribonucleoside analogues 2a,b have been efficiently synthesized from commercial 1-O-methyl-2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentofuranose. The conversion of these nucleosides to the phosphoramidite derivatives 13a,b and 14a,b for subsequent incorporation into oligodeoxyribonucleotide analogues is also described.

  DOI：

  10.1016/0960-894x(95)00589-l

文献信息

• Novel 1′-homo-<i>N</i>-2′-deoxy-α-nucleosides: synthesis, characterization and biological activity
  作者：Alejandro Carnero、Virginia Martín-Nieves、Yogesh S. Sanghvi、Olivia O. Russel、Leda Bassit、Raymond F. Schinazi、Susana Fernández、Miguel Ferrero

  DOI：10.1039/d0ra03254a

  日期：——

  single crystal X-ray structure of 1′-homo-N-2′-deoxy-α-adenosine and NMR studies. The biological activity of these 1′-homo-N-2′-deoxy-α-nucleosides as antiviral (HIV-1 and HBV) and cytotoxic studies was measured in multiple cell systems. The unique structure and easy accessibility of these compounds may allow their use in the design of new nucleoside analogs with potential biological activity and as a scaffold

  首次以有效的方式合成了一系列含有天然核碱基以及 5-氟和 5-碘嘧啶类似物的新型 1'-同型-N -2'-脱氧-α-核苷。此外，已经完成了用于组装含有两个与单个嘧啶碱基的N -1 和N -3 位置连接的糖部分的二聚支架的高产率方案。新型同核苷的结构是通过 1'-高-N -2'-脱氧-α-腺苷的单晶 X 射线结构和 NMR 研究确定的。这些 1'-同型N的生物活性-2'-脱氧-α-核苷作为抗病毒药物（HIV-1 和 HBV）和细胞毒性研究在多个细胞系统中进行了测量。这些化合物的独特结构和易获得性可能允许它们用于设计具有潜在生物活性的新核苷类似物，并作为组合化学的支架。
• Synthesis of (2-Deoxy-α- and -β-<scp>d</scp>-<i>erythro</i>-pentofuranosyl)(thymin-1-yl)alkanes and Their Incorporation into Oligodeoxyribonucleotides. Effect of Nucleobase−Sugar Linker Flexibility on the Formation of DNA−DNA and DNA−RNA Hybrids
  作者：Jila H. Boal、Andrzej Wilk、Carlo L. Scremin、Glenn N. Gray、Lawrence R. Phillips、Serge L. Beaucage

  DOI：10.1021/jo961548k

  日期：1996.1.1

  On the basis of modeling studies, the (2-deoxy-alpha- and beta-D-erythro-pentofuranosyl) (thymin-1-yl) alkanes 1a,b and 2a,b were selected as potential conformational probes for altDNA oligonucleotides. A straightforward approach to the synthesis of 1a,b and 2a,b from commercial 2-deoxy-D-ribose (3) and 1-O-methyl-2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentofuranose (13), respectively, was developed. These nucleoside analogues were converted to the phosphoramidite derivatives 27a,b-30a,b and incorporated into oligonucleotide 31 at predetermined sites and defined internucleotidic motifs. The insertion of 1a,b according to either a (3' --> 5')- or a (3' --> 3')-internucleotidic polarity produced oligonucleotides exhibiting a slightly higher affinity for their complementary unmodified DNA sequence than for the corresponding RNA sequence (Table 3). Conversely, the incorporation of 2a into 31 according to a (3' --> 3')-orientation generated, for the first time, an altDNA oligonucleotide displaying a greater affinity for its complementary unmodified RNA sequence (Delta T-m = 6 degrees C) than for the corresponding DNA sequence (Delta T-m = 10 degrees C). thermodynamically less stable than the duplex having unmodified alpha-2'-deoxythymidine similarly incorporated into 31 (Delta Delta T-m = 3 degrees C).
• [(2-Deoxy-α- and β-D-erythro-pentofuranosyl)thymin-1-YL] methane derivatives as potential conformational probes for altDNA oligonucleotides
  作者：Carlo L. Scremin、Jila H. Boal、Andrzej Wilk、Lawrence R. Phillips、Serge L. Beaucage

  DOI：10.1016/0960-894x(95)00589-l

  日期：1996.1

  The previously unknown deoxyribonucleoside analogues 2a,b have been efficiently synthesized from commercial 1-O-methyl-2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentofuranose. The conversion of these nucleosides to the phosphoramidite derivatives 13a,b and 14a,b for subsequent incorporation into oligodeoxyribonucleotide analogues is also described.