N-[1-[(2R,4S,5R)-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphinothioyl]oxymethyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide | 224186-63-4

• 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: N-[1-[(2R,4S,5R)-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphinothioyl]oxymethyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 224186-63-4
• 化学式: C₅₀H₅₁N₆O₁₃PS
• 分子量: 1007.03
• InChiKey: TYMNDQIVUDWWEX-YWSSKRSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  71
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  261
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 N-[1-[(2R,4S,5R)-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphinothioyl]oxymethyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 [(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-3-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]methoxy-[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)-sulfidophosphanium
  参考文献：
  名称：

  Synthesis of Dimer Phosphoramidite Synthons for Oligodeoxyribonucleotide Phosphorothioates Using Diethyldithiocarbonate disulfide as an Efficient Sulfurizing Reagent

  摘要：

  An efficient solution phase synthesis of deoxyribonucleoside phosphorothioate dimers utilizing phosphoramidite approach is described. Diethyldithiocarbonate disulfide (DDD) was found to be an efficient sulfurizing reagent in the conversion of phosphite triesters to phosphorothioate triesters.

  DOI：

  10.1080/07328319908044844
• 作为产物：
  描述：

  N4-苯甲酰基-5′-O-(4,4′-二甲氧基三苯基)-2′-脱氧胞苷 在 四氮唑 、 diethyldithiocarbonate disulfide 、 对甲苯磺酸 、 一水合肼 作用下， 以 吡啶 、 甲醇 、 溶剂黄146 、 乙酸乙酯 、 乙腈 为溶剂， 反应 6.0h， 生成 N-[1-[(2R,4S,5R)-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphinothioyl]oxymethyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
  参考文献：
  名称：

  Oligodeoxyribonucleotide Phosphorothioates: Substantial Reduction of (N-1)-mer Content Through the Use of Trimeric Phosphoramidite Synthons

  摘要：

  Use of fully protected trimeric phosphoramidite synthons in the synthesis of oligonucleotide phosphorothioate shows a substantial reduction (>85%) in (n-1)-mer content as compared to oligomers synthesized through coupling of standard phosphoramidite monomers. A 20-mer oligodeoxyribonucleotide phosphorothioate which is in phase I clinical trials was chosen as an example for the studies.

  DOI：

  10.1080/15257779908043091

文献信息

• Investigation of a Facile Synthetic Method for Phosphorothioate Dimer Synthons In Oligonucleotide Phosphorothioates Synthesis
  作者：Takanori Miyashita、Kohei Yamada、Kazuhiko Kondo、Kenya Mori、Kazuo Shinozuka

  DOI：10.1080/15257770008033035

  日期：2000.5

  A facile synthetic method of a phosphorothioate dimer block was investigated. Dinucleoside phosphite triester intermediates were obtained in one-pot synthesis by the coupling of a protected nucleoside bearing free 5'-OH and a protected nucleoside bearing free 3'-OH in the presence of phosphorous trichloride (PCl3) and 1,2,4-triazole. The intermediates were easily sulfurized to afford the desired phosphorothioate dimer blocks in 33-64% overall yields.