1-[(2R,4R,5R)-5-[2-[1,1-diethoxyethyl(ethoxy)phosphoryl]ethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione | 171336-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(2R,4R,5R)-5-[2-[1,1-diethoxyethyl(ethoxy)phosphoryl]ethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 171336-66-6
• 化学式: C₁₉H₃₃N₂O₈P
• 分子量: 448.453
• InChiKey: VYTBXSSYAFIHFZ-XEOLWWRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[(2R,4R,5R)-5-[2-[1,1-diethoxyethyl(ethoxy)phosphoryl]ethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 三甲基氯硅烷 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  摘要：

  Chimeric DNA molecules containing four different linking groups, the natural phosphate, 5'-methylenephosphonate. bis(methylene)phosphinate, and bis(methylene) sulfone (see Fig.1), were directly compared for their ability to form duplexes with complementary DNA and DNA chimeras. From melting temperatures for analogous complementary sequences, general conclusions about the impact of geometric distortion of the internucleotide linkage around the two P-O-C bridges were drawn, as were conclusions about the impact on duplex stability that arises from the removal of the negative charge in the linking group. Each structural perturbation diminished the melting temperature, by ca. -2.5degrees per modification for the 5'-methylenephosphonate, -3.5degrees per modification for the bis(methylene)phosphinate, and -4.5degrees per modification for the bis(methylene) sulfone linker. These results have implications for DNA chemistry including the design of 'antisense' candidates and the proposal of alternative genetic materials in the search for non-terrean life.

  DOI：

  10.1002/1522-2675(200209)85:9<2777::aid-hlca2777>3.0.co;2-1
• 作为产物：
  描述：

  diethyl (1,1-diethoxyethyl)phosphonate 、 3',4'-anhydrothymidine 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以100%的产率得到1-[(2R,4R,5R)-5-[2-[1,1-diethoxyethyl(ethoxy)phosphoryl]ethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  摘要：

  Chimeric DNA molecules containing four different linking groups, the natural phosphate, 5'-methylenephosphonate. bis(methylene)phosphinate, and bis(methylene) sulfone (see Fig.1), were directly compared for their ability to form duplexes with complementary DNA and DNA chimeras. From melting temperatures for analogous complementary sequences, general conclusions about the impact of geometric distortion of the internucleotide linkage around the two P-O-C bridges were drawn, as were conclusions about the impact on duplex stability that arises from the removal of the negative charge in the linking group. Each structural perturbation diminished the melting temperature, by ca. -2.5degrees per modification for the 5'-methylenephosphonate, -3.5degrees per modification for the bis(methylene)phosphinate, and -4.5degrees per modification for the bis(methylene) sulfone linker. These results have implications for DNA chemistry including the design of 'antisense' candidates and the proposal of alternative genetic materials in the search for non-terrean life.

  DOI：

  10.1002/1522-2675(200209)85:9<2777::aid-hlca2777>3.0.co;2-1

文献信息

• ——
  作者：Daniel Hutter、Monika O. Blaettler、Steven A. Benner

  DOI：10.1002/1522-2675(200209)85:9<2777::aid-hlca2777>3.0.co;2-1

  日期：2002.9

  Chimeric DNA molecules containing four different linking groups, the natural phosphate, 5'-methylenephosphonate. bis(methylene)phosphinate, and bis(methylene) sulfone (see Fig.1), were directly compared for their ability to form duplexes with complementary DNA and DNA chimeras. From melting temperatures for analogous complementary sequences, general conclusions about the impact of geometric distortion of the internucleotide linkage around the two P-O-C bridges were drawn, as were conclusions about the impact on duplex stability that arises from the removal of the negative charge in the linking group. Each structural perturbation diminished the melting temperature, by ca. -2.5degrees per modification for the 5'-methylenephosphonate, -3.5degrees per modification for the bis(methylene)phosphinate, and -4.5degrees per modification for the bis(methylene) sulfone linker. These results have implications for DNA chemistry including the design of 'antisense' candidates and the proposal of alternative genetic materials in the search for non-terrean life.