1-[[(2S,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(hydroxymethyl)oxolan-2-yl]methyl]-5-methylpyrimidine-2,4-dione | 175544-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-[[(2S,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(hydroxymethyl)oxolan-2-yl]methyl]-5-methylpyrimidine-2,4-dione
• CAS: 175544-04-4
• 化学式: C₃₂H₃₄N₂O₇
• 分子量: 558.631
• InChiKey: RFJIRPSLFVYBRJ-YTCPBCGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 1-[[(2S,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(hydroxymethyl)oxolan-2-yl]methyl]-5-methylpyrimidine-2,4-dione 在 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-[[(2R,3S,5S)-3-[bis(4-methoxyphenyl)-phenylmethoxy]-5-[(5-methyl-2,4-dioxopyrimidin-1-yl)methyl]oxolan-2-yl]methoxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  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 咪唑 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 氢氧化钾 、 硼烷 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 36.17h， 生成 1-[[(2S,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(hydroxymethyl)oxolan-2-yl]methyl]-5-methylpyrimidine-2,4-dione
  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

• 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.