[(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]oxolan-3-yl] 4-oxopentanoate | 224186-73-6

• 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: [(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]oxolan-3-yl] 4-oxopentanoate
• CAS: 224186-73-6
• 化学式: C₅₅H₅₇N₆O₁₅P
• 分子量: 1073.06
• InChiKey: MIBMSUXYDWPNGH-ITSGNLPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  77
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  252
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]oxolan-3-yl] 4-oxopentanoate 在 sulfur 、 一水合肼 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 0.67h， 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：

  Investigation of a Facile Synthetic Method for Phosphorothioate Dimer Synthons In Oligonucleotide Phosphorothioates Synthesis

  摘要：

  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.

  DOI：

  10.1080/15257770008033035
• 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 、 对甲苯磺酸 作用下， 以 甲醇 、 乙酸乙酯 、 乙腈 为溶剂， 反应 5.0h， 生成 [(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]oxolan-3-yl] 4-oxopentanoate
  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