1-(2-deoxy-β-D-erythro-pentofuranosyl)-2-(thymin-1-yl)ethane | 173935-27-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-deoxy-β-D-erythro-pentofuranosyl)-2-(thymin-1-yl)ethane
• 英文别名: 1-[2-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]ethyl]-5-methylpyrimidine-2,4-dione
• CAS: 173935-27-8
• 化学式: C₁₂H₁₈N₂O₅
• 分子量: 270.285
• InChiKey: SXGVSXJQOOMYSF-LPEHRKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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-(2-deoxy-β-D-erythro-pentofuranosyl)-2-(thymin-1-yl)ethane 在 4-二甲氨基吡啶 、 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 5.0h， 生成
  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：

  (4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,4-diol 在 ammonium hydroxide 、 dimethyl sulfide borane 、 sodium hydride 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 25.0h， 生成 1-(2-deoxy-β-D-erythro-pentofuranosyl)-2-(thymin-1-yl)ethane
  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