(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)(thymin-1-yl) methane | 175672-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)(thymin-1-yl) methane
• CAS: 175672-61-4
• 化学式: C₂₇H₂₈N₂O₇
• 分子量: 492.529
• InChiKey: RYCASZUHTTVFRD-XPWALMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  116.69
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)(thymin-1-yl) methane 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 2'-deoxy-1'-homothymidine
  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：

  3-甲氧基-2-甲基丙-2-烯酰异氰酸酯 在 盐酸 、 溶剂黄146 、 三乙胺 作用下， 以 苯 为溶剂， 反应 32.0h， 生成 (2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)(thymin-1-yl) methane
  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

文献信息

• [(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.