1-[(3'S,4'R)-3'-O-benzoyl-2',5',6'-trideoxy-6'-(diethoxyphosphinyl)-β-hexofuranosyl]thymine | 500018-96-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 1-[(3'S,4'R)-3'-O-benzoyl-2',5',6'-trideoxy-6'-(diethoxyphosphinyl)-β-hexofuranosyl]thymine
• 英文别名: 1-[(3S,4R)-3-O-benzoyl-6-(diethoxyphosphinyl)-2,5,6-trideoxy-β-hexofuranosyl]thymine
• CAS: 500018-96-2
• 化学式: C₂₂H₂₉N₂O₈P
• 分子量: 480.455
• InChiKey: SAWUNBZOAXRFHV-CEXWTWQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125.92
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-[(3'S,4'R)-3'-O-benzoyl-2',5',6'-trideoxy-6'-(diethoxyphosphinyl)-β-hexofuranosyl]thymine 在 苯甲基-2-磺酰三硝基三氮唑 、 lithium bromide 作用下， 以 吡啶 为溶剂， 反应 172.0h， 生成 2'-deoxy-O^P-ethyl-5'-O-(4,4'-dimethoxytrityl)thymidylylmethylene-(3'->5')-3'-O-benzoyl-2',5'-dideoxythymidine
  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：

  3',4'-anhydrothymidine 在 正丁基锂 、 偶氮二甲酸二异丙酯 、 三氟化硼乙醚 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 24.0h， 生成 1-[(3'S,4'R)-3'-O-benzoyl-2',5',6'-trideoxy-6'-(diethoxyphosphinyl)-β-hexofuranosyl]thymine
  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

• Photoredox-Catalyzed Deformylative 1,4-Addition of 2′-Deoxy-5′-<i>O</i>-phthalimidonucleosides for Synthesis of 5′-Carba Analogs of Nucleoside 5′-Phosphates
  作者：Yuta Ito、Airi Kimura、Takashi Osawa、Yoshiyuki Hari

  DOI：10.1021/acs.joc.8b00637

  日期：2018.9.21

  approach for the synthesis of the 5′-carba analogs of nucleoside 5′-phosphates from 2′-deoxy-5′-O-phthalimidonucleosides by a visible-light-mediated deformylative 1,4-addition was developed. This method enabled rapid and facile generation of 4′-carbon radicals of nucleosides. Moreover, this synthetic strategy was applicable to the 5′-carba analogs of nucleoside 5′-phosphates as well as other 5′-carba nucleosides

  开发了一种简明的方法，该方法通过可见光介导的脱甲酰基1，4-加成从2'-脱氧-5' - O-邻苯二甲酰亚胺核苷合成核苷5'-磷酸的5'-carba类似物。该方法使得能够快速且容易地生成核苷的4'-碳自由基。而且，该合成策略适用于核苷5'-磷酸的5'-carba类似物以及其他带有甲氧基羰基，氰基和N-甲基氨磺酰基的5'-carba核苷。