3'-O-adamantaneacetyl-N³-pivaloyloxymethylthymidine | 913697-70-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-O-adamantaneacetyl-N³-pivaloyloxymethylthymidine
• 英文别名: 3'-adamantylacetyl-N³-pivaloyloxymethylthymidine；[3-[(2R,4S,5R)-4-[2-(1-adamantyl)acetyl]oxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]methyl 2,2-dimethylpropanoate
• CAS: 913697-70-8
• 化学式: C₂₈H₄₀N₂O₈
• 分子量: 532.634
• InChiKey: ZDIVAEVLOAUKMT-JUEKQWEISA-N

物化性质

• 熔点：
  63-68 °C
• 沸点：
  636.4±65.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  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 、 吡啶 、 碘 作用下， 以 乙腈 、 四氢呋喃 为溶剂， 反应 0.58h， 生成
  参考文献：
  名称：

  Simple and Efficient Solution-Phase Synthesis of Oligonucleotides Using Extractive Work-Up

  摘要：

  A solution-phase synthesis protocol amenable to scale-up was developed for the preparation of oligonucleotides employing phosphoramidite chemistry and DMTr/iBu/Bz-protected monomers. Isolation of intermediates was accomplished by means of extractions as the only purification tool. The potential of the method is demonstrated with the synthesis of a hexameric DNA fragment in high yield and purity.

  DOI：

  10.1021/op060133q
• 作为产物：
  描述：

  保护胸苷 在 三乙基硅烷 、 二氯乙酸 、 4-二甲氨基吡啶 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 3'-O-adamantaneacetyl-N³-pivaloyloxymethylthymidine
  参考文献：
  名称：

  Simple and Efficient Solution-Phase Synthesis of Oligonucleotides Using Extractive Work-Up

  摘要：

  A solution-phase synthesis protocol amenable to scale-up was developed for the preparation of oligonucleotides employing phosphoramidite chemistry and DMTr/iBu/Bz-protected monomers. Isolation of intermediates was accomplished by means of extractions as the only purification tool. The potential of the method is demonstrated with the synthesis of a hexameric DNA fragment in high yield and purity.

  DOI：

  10.1021/op060133q

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.