1-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(2-thioxo-2λ⁵-[1,3,2]dithiaphospholan-2-yloxy)-tetrahydro-furan-2-yl]-4-[1-methyl-pyrrolidin-(2Z)-ylideneamino]-1H-pyrimidin-2-one | 172033-38-4

• 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-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(2-thioxo-2λ⁵-[1,3,2]dithiaphospholan-2-yloxy)-tetrahydro-furan-2-yl]-4-[1-methyl-pyrrolidin-(2Z)-ylideneamino]-1H-pyrimidin-2-one
• 英文别名: 1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[(2-sulfanylidene-1,3,2lambda5-dithiaphospholan-2-yl)oxy]oxolan-2-yl]-4-[(1-methylpyrrolidin-2-ylidene)amino]pyrimidin-2-one；1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[(2-sulfanylidene-1,3,2λ5-dithiaphospholan-2-yl)oxy]oxolan-2-yl]-4-[(1-methylpyrrolidin-2-ylidene)amino]pyrimidin-2-one
• CAS: 172033-38-4
• 化学式: C₃₇H₄₁N₄O₆PS₃
• 分子量: 764.927
• InChiKey: XBTKEYUACXLHOI-GTXBZULCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  51
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  177
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(2-thioxo-2λ⁵-[1,3,2]dithiaphospholan-2-yloxy)-tetrahydro-furan-2-yl]-4-[1-methyl-pyrrolidin-(2Z)-ylideneamino]-1H-pyrimidin-2-one 在 1,2-环氧丁烷 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2'-deoxycytidine homodimer
  参考文献：
  名称：

  Synthesis of Oligo(Deoxyribonucleoside Phosphorodithioate)s by the Dithiaphospholane Approach

  摘要：

  A novel method of synthesis of oligo(deoxyribonucleoside phosphorodithioate)s (S-2-ODNs), based on the ring-opening condensation of nucleoside 3'-0-(2-thiono-1,3,2-dithiaphospholane)s with 5'-O-deprotected nucleosi(ti)des in the presence of a strong organic base such as DBU, is presented. The process has been adapted to the requirements of automated solid-phase oligonucleotide synthesis with a relatively short condensation step (5 min) and reasonable step-yield(>95%). N-Methylpyrrolidin-2-ylidenyl (Pya) was found to be the group of choice for the protection of reactive aminofunctions of nucleobases in nucleotide substrates. Sarcosine-containing linker (LCA CPG SAR) was employed due to its known resistance to cleavage by DBU. Several medium-size S-2-ODNs were prepared by this approach. Their identity and purity was confirmed by means of P-31 NMR, gel electrophoresis, and mass spectrometry. It has been demonstrated that, contrary to a recent report, S-2-ODNs are not degraded by DNaseI.

  DOI：

  10.1021/jo00126a060
• 作为产物：
  描述：

  2-(N,N-diisopropylamino)-1,3,2-dithiaphospholane 、 5'-O-(di-p-methoxytrityl)-4-N-(N-methylpyrrolidin-2-ylidene)-2'-deoxycytidine 在 四氮唑 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 生成 1-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(2-thioxo-2λ⁵-[1,3,2]dithiaphospholan-2-yloxy)-tetrahydro-furan-2-yl]-4-[1-methyl-pyrrolidin-(2Z)-ylideneamino]-1H-pyrimidin-2-one
  参考文献：
  名称：

  Synthesis of Oligo(Deoxyribonucleoside Phosphorodithioate)s by the Dithiaphospholane Approach

  摘要：

  A novel method of synthesis of oligo(deoxyribonucleoside phosphorodithioate)s (S-2-ODNs), based on the ring-opening condensation of nucleoside 3'-0-(2-thiono-1,3,2-dithiaphospholane)s with 5'-O-deprotected nucleosi(ti)des in the presence of a strong organic base such as DBU, is presented. The process has been adapted to the requirements of automated solid-phase oligonucleotide synthesis with a relatively short condensation step (5 min) and reasonable step-yield(>95%). N-Methylpyrrolidin-2-ylidenyl (Pya) was found to be the group of choice for the protection of reactive aminofunctions of nucleobases in nucleotide substrates. Sarcosine-containing linker (LCA CPG SAR) was employed due to its known resistance to cleavage by DBU. Several medium-size S-2-ODNs were prepared by this approach. Their identity and purity was confirmed by means of P-31 NMR, gel electrophoresis, and mass spectrometry. It has been demonstrated that, contrary to a recent report, S-2-ODNs are not degraded by DNaseI.

  DOI：

  10.1021/jo00126a060