5'-O-(4,4'-dimethoxytrityl)-N2-isobutyryl-deoxyguanosine-3'-O-(2-selena-spiro-4,4-pentamethylene-1,3,2-oxathiaphospholane) | 912262-43-2

• 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: 5'-O-(4,4'-dimethoxytrityl)-N2-isobutyryl-deoxyguanosine-3'-O-(2-selena-spiro-4,4-pentamethylene-1,3,2-oxathiaphospholane)
• 英文别名: 5'-O-(4,4'-dimethoxytrityl)-N²-isobutyryl-deoxyguanosine-3'-O-(2-selena-spiro-4,4-pentamethylene-1,3,2-oxathiaphospholane)
• CAS: 912262-43-2
• 化学式: C₄₂H₄₈N₅O₈PSSe
• 分子量: 892.872
• InChiKey: NJSPBGAZCYFBIK-VHJLYONSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.73
• 重原子数：
  58.0
• 可旋转键数：
  13.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  148.05
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-N2-isobutyryl-deoxyguanosine-3'-O-(2-selena-spiro-4,4-pentamethylene-1,3,2-oxathiaphospholane) 、 二苯氨基甲酰氯 在 吡啶 、 N,N-二异丙基乙胺 作用下， 反应 1.0h， 以66%的产率得到5'-O-(4,4'-dimethoxytrityl)-N²-isobutyryl-O⁶-diphenylcarbamoyl-deoxyguanosine-3'-O-(2-selena-spiro-4,4-pentamethylene-1,3,2-oxathiaphospholane)
  参考文献：
  名称：

  Oxathiaphospholane Approach to the Synthesis of Oligodeoxyribonucleotides Containing Stereodefined Internucleotide Phosphoroselenoate Function

  摘要：

  5'-O-DMT-deoxyribonucleoside-3'-O-(2-selena-4,4-pentamethylene-1,3,2-oxathiaphospholane) monomers, derivatives of dA, dC, dG, and T, can be resolved into pure P-diastereomers by silica gel column chromatography. They have been used for DBU-promoted, either solution- or solid-phase synthesis of P-stereodefined phosphoroselenoate analogues of oligodeoxyribonucleotides. Fast- and slow-eluting monomers are precursors of phosphoroselenoate internucleotide linkage of R-p and S-p absolute configuration, respectively.

  DOI：

  10.1021/ol051302e
• 作为产物：
  描述：

  2-chloro-4,4-pentamethylene-1,3,2-oxathiaphospholane 在 selenium 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 12.25h， 生成 5'-O-(4,4'-dimethoxytrityl)-N2-isobutyryl-deoxyguanosine-3'-O-(2-selena-spiro-4,4-pentamethylene-1,3,2-oxathiaphospholane)
  参考文献：
  名称：

  Oxathiaphospholane Approach to the Synthesis of Oligodeoxyribonucleotides Containing Stereodefined Internucleotide Phosphoroselenoate Function

  摘要：

  5'-O-DMT-deoxyribonucleoside-3'-O-(2-selena-4,4-pentamethylene-1,3,2-oxathiaphospholane) monomers, derivatives of dA, dC, dG, and T, can be resolved into pure P-diastereomers by silica gel column chromatography. They have been used for DBU-promoted, either solution- or solid-phase synthesis of P-stereodefined phosphoroselenoate analogues of oligodeoxyribonucleotides. Fast- and slow-eluting monomers are precursors of phosphoroselenoate internucleotide linkage of R-p and S-p absolute configuration, respectively.

  DOI：

  10.1021/ol051302e