N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[(2-sulfanylidene-1,3,2lambda5-dithiaphospholan-2-yl)oxy]oxolan-2-yl]purin-6-yl]benzamide | 145498-68-6

• 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: N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[(2-sulfanylidene-1,3,2lambda5-dithiaphospholan-2-yl)oxy]oxolan-2-yl]purin-6-yl]benzamide
• 英文别名: N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[(2-sulfanylidene-1,3,2λ5-dithiaphospholan-2-yl)oxy]oxolan-2-yl]purin-6-yl]benzamide
• CAS: 145498-68-6
• 化学式: C₄₀H₃₈N₅O₆PS₃
• 分子量: 811.943
• InChiKey: HXACUJBEWCRPCC-BMPTZRATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  55
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  202
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[(2-sulfanylidene-1,3,2lambda5-dithiaphospholan-2-yl)oxy]oxolan-2-yl]purin-6-yl]benzamide 在 ammonium hydroxide 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 5.25h， 生成 O-(2'-deoxyadenosin-3'-yl) phosphorodithioate triethylammonium salt
  参考文献：
  名称：

  Efficient One-Pot Synthesis of 2‘-Deoxyribonucleoside 3‘-O- and 5‘-O-Phosphorodithioates

  摘要：

  DOI：

  10.1021/jo961801g
• 作为产物：
  描述：

  2-(N,N-diisopropylamino)-1,3,2-dithiaphospholane 、 N6-苯甲酰基-5'-O-(4,4'-二甲氧基三苯基)-2'-脱氧腺苷 在 四氮唑 、 sulfur 作用下， 生成 N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[(2-sulfanylidene-1,3,2lambda5-dithiaphospholan-2-yl)oxy]oxolan-2-yl]purin-6-yl]benzamide
  参考文献：
  名称：

  二硫代磷烷法合成二-和寡聚（脱氧核糖核苷二硫代磷酸酯）

  摘要：

  通过使固相结合的核苷与核苷5'反应，合成了4种二核苷二硫代磷酸酯：T PS2 T（1a），d（C PS2 C）（1b），d {A PS2 A}和d（G PS2 G）（1d）。在DBU存在下，-O-DMT-3'-O-（2-硫代-1,3,2-二硫代膦酸酯）（2a-d）。通过该方法获得了没有硫代磷酸酯污染的嘧啶五聚体。

  DOI：

  10.1016/s0040-4039(00)60831-6

文献信息

• The synthesis of Di- and oligo(deoxyribonucleoside phosphorodithioates) by dithiaphospholane method
  作者：Andrzej Okruszek、Agnieszka Sierzchala、Marek Sochacki、Wojciech J. Stec

  DOI：10.1016/s0040-4039(00)60831-6

  日期：——

  Four dinucleoside phosphorodithioates: TPS2T (1a), d(CPS2C) (1b), dAPS2A} and d(GPS2G) (1d) were synthesized by reacting solid support-bound nucleosides with nucleoside 5′-O-DMT-3′-O-(2-thio-1,3,2-dithiaphospholanes) (2a-d) in the presence of DBU. Pyrimidine pentamers, free from phosphorothioate contamination, were obtained by this method.

  通过使固相结合的核苷与核苷5'反应，合成了4种二核苷二硫代磷酸酯：T PS2 T（1a），d（C PS2 C）（1b），d A PS2 A}和d（G PS2 G）（1d）。在DBU存在下，-O-DMT-3'-O-（2-硫代-1,3,2-二硫代膦酸酯）（2a-d）。通过该方法获得了没有硫代磷酸酯污染的嘧啶五聚体。
• Synthesis of Oligo(Deoxyribonucleoside Phosphorodithioate)s by the Dithiaphospholane Approach
  作者：Andrzej Okruszek、Agnieszka Sierzcha-la、Karen L. Fearon、Wojciech J. Stec

  DOI：10.1021/jo00126a060

  日期：1995.10

  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.
• Efficient One-Pot Synthesis of 2‘-Deoxyribonucleoside 3‘-<i>O</i>- and 5‘-<i>O</i>-Phosphorodithioates
  作者：Andrzej Okruszek、Magdalena Olesiak、Danuta Krajewska、Wojciech J. Stec

  DOI：10.1021/jo961801g

  日期：1997.4.1