[3-[(2R,4S,5R)-4-[2-(1-adamantyl)acetyl]oxy-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[3-(2,2-dimethylpropanoyloxymethyl)-5-methyl-2,4-dioxopyrimidin-1-yl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]methyl 2,2-dimethylpropanoate | 1032047-31-6

• 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: [3-[(2R,4S,5R)-4-[2-(1-adamantyl)acetyl]oxy-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[3-(2,2-dimethylpropanoyloxymethyl)-5-methyl-2,4-dioxopyrimidin-1-yl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]methyl 2,2-dimethylpropanoate
• CAS: 1032047-31-6
• 化学式: C₆₈H₈₄N₅O₁₈P
• 分子量: 1290.41
• InChiKey: ZLAIPRPWHBQWCY-ZUCPRVCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  92
• 可旋转键数：
  30
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  258
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  3'-O-adamantaneacetyl-N³-pivaloyloxymethylthymidine 、 5'-O-dimethoxytrityl-N³-pivaloyloxymethylthymidine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 在 4,5-二氰基咪唑 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 、 [3-[(2R,4S,5R)-4-[2-(1-adamantyl)acetyl]oxy-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[3-(2,2-dimethylpropanoyloxymethyl)-5-methyl-2,4-dioxopyrimidin-1-yl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphanyl]oxymethyl]oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  A two-step sulfurization for efficient solution-phase synthesis of phosphorothioate oligonucleotides

  摘要：

  A solution-phase approach for the synthesis of phosphorothioate oligonucleotides that circumvents the use of chromatographic purifications of protected phosphorothioate intermediates was developed. Implementation of a two-step sulfurization protocol in the phosphoramidite method allows efficient isolation of the intermediate phosphorothioates by extractions. The viability of this approach is demonstrated by the synthesis of a hexameric phosphorothioate oligonucleotide fragment. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.025

文献信息

• A two-step sulfurization for efficient solution-phase synthesis of phosphorothioate oligonucleotides
  作者：Amar B.T. Ghisaidoobe、Martijn C. de Koning、Howard I. Duynstee、Paul B.W. Ten Kortenaar、Herman S. Overkleeft、Dmitri V. Filippov、Gijs A. van der Marel

  DOI：10.1016/j.tetlet.2008.03.025

  日期：2008.5

  A solution-phase approach for the synthesis of phosphorothioate oligonucleotides that circumvents the use of chromatographic purifications of protected phosphorothioate intermediates was developed. Implementation of a two-step sulfurization protocol in the phosphoramidite method allows efficient isolation of the intermediate phosphorothioates by extractions. The viability of this approach is demonstrated by the synthesis of a hexameric phosphorothioate oligonucleotide fragment. (C) 2008 Elsevier Ltd. All rights reserved.