2'-deoxy-3'-de(phosphinicooxy)thymidylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine | 452304-74-4

• 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: 2'-deoxy-3'-de(phosphinicooxy)thymidylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine
• 英文别名: 1-[(2R,4S,5S)-5-(hydroxymethyl)-4-[2-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]ethylsulfonylmethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 452304-74-4
• 化学式: C₂₂H₃₀N₄O₁₀S
• 分子量: 542.567
• InChiKey: YCRMFVYRSXYBSH-SISKNIMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  200
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2'-deoxy-3'-de(phosphinicooxy)thymidylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine 在 4-二甲氨基吡啶 、 二异丙基铵盐四氮唑 、 三乙胺 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 5.0h， 生成 2'-deoxy-3'-de(phosphinicooxy)-5'-O-(4,4'-dimethoxytrityl)thymidylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine 3'-(2-cyanoethyl diisopropylphosphoramidite)
  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：

  1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine 在 Oxone 、 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 氢氟酸 、 sodium acetate 、 caesium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 2'-deoxy-3'-de(phosphinicooxy)thymidylylmethylenesulfonylmethylene-(3'->5')-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