3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-allyluridine | 143463-63-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-allyluridine
• 英文别名: 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-allyluridine；3’,5’-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2’-O-allyluridine；1-[(6aR,8R,9R,9aR)-2,2,4,4-tetra(propan-2-yl)-9-prop-2-enoxy-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]pyrimidine-2,4-dione
• CAS: 143463-63-2
• 化学式: C₂₄H₄₂N₂O₇Si₂
• 分子量: 526.778
• InChiKey: GKPCPKCACLXXGP-JMJGKCIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  101.01
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-allyluridine 在 吡啶 、 sodium dithionite 、 四丁基氟化铵 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  作为RNA型分子的2'-修饰的二氟膦酰化烯丙基醚部分：合成，热和代谢研究。

  摘要：

  描述了寡核苷酸的首次合成，该寡核苷酸将U RF掺入了尿素，该尿素经二氟膦酰化的烯丙基醚修饰到2'位置。可以有效地制备氟化脲醛酸酯和miR-342-3p类似物。紫外熔解实验和酶促降解研究表明，这一系列新的氟化寡核苷酸显示出良好的和热代谢稳定性以及增加的亲脂性。与含有2'- O-烯丙啶代替U RF的寡核苷酸的比较表明，这些化学性质的改善与二氟甲基膦酸酯基团的存在有关。

  DOI：

  10.1021/acs.orglett.9b01689
• 作为产物：
  描述：

  3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-allyl-O⁴-(2-nitrophenyl)uridine 在 四甲基胍 、 2-硝基苯甲醛肟 作用下， 以85%的产率得到3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-allyluridine
  参考文献：
  名称：

  Synthesis of Modified Nucleotide Building Blocks Containing Electrophilic Groups in the 2′-Position

  摘要：

  Chemical syntheses of 2'-O-(allyloxycarbonyl)methyladenosine, 2'-O(methoxycarbonyl)methyladenosine and 2'-O-(2,3-dibenzoyloxy)propyluridine 3'-2-cyanoethyl-N,N-diisopropyl phosphoramidite building blocks are described. These monomers were used successfully to incorporate carboxylic acid, 1,2-diol and aldehyde functionalities into synthetic oligonucleotides.

  DOI：

  10.1080/15257770008045453

文献信息

• ——
  作者：T. S. Zatsepin、A. V. Kachalova、E. A. Romanova、D. A. Stetsenko、M. J. Gait、T. S. Oretskaya

  DOI：10.1023/a:1009579002330

  日期：——

  A new uridine derivative, 2'-O-(2,3-dihydroxypropyl)uridine, and its 3'-phosphoramidite were obtained for direct introduction into oligonucleotides during automated chemical synthesis. Oligonucleotides 10 to 15 nt long harboring 2'-O-(2,3-dihydroxypropyl)uridine residues were synthesized; periodate oxidation of these oligomers gave oligonucleotides containing 2'-O-(2-oxoethyl)uridine residues. The

  获得了新的尿苷衍生物2'-O-（2,3-二羟丙基）尿苷及其3'-亚磷酰胺，用于在自动化化学合成过程中直接引入寡核苷酸。合成了具有2'-O-（2,3-二羟丙基）尿苷残基的10-15 nt长的寡核苷酸；这些低聚物的高碘酸盐氧化得到含有2'-O-（2-氧代乙基）尿苷残基的寡核苷酸。通过与对硝基苯基肼和甲硫氨酸甲酯的相互作用证实了在碳水化合物部分的2'位置上存在反应性醛基。含有修饰单元的DNA双链体的热稳定性与天然类似物几乎没有区别。
• Dinucleotides containing two allyl groups by combinations of allyl phosphotriesters, 5-allyl-, 2′-O-allyl- and 2′-arabino-O-allyl uridine derivatives as substrates for ring-closing metathesis
  作者：Philip Børsting、Morten Freitag、Poul Nielsen

  DOI：10.1016/j.tet.2004.09.023

  日期：2004.11

  Five different dinucleotides, each containing two allyl groups in various positions, were prepared and studied as substrates for ring-closing metathesis reactions. These dinucleotides were designed from appropriate nucleoside building blocks combining four different positions for the allyl group; the allyl phosphotriester linkage, 5-allyl-2' -deoxyuridine, and ribo- as well as arabino-configured 2'-O-allyluridine. Thus, convenient procedures for these building blocks were developed. From the dinucleotides, two new cyclic nucleotide structures were obtained; one connecting two adjacent nucleobase moieties and the other forming an unsaturated four-carbon linkage between the phosphate moiety and the adjacent pyrimidine nucleobase. The latter cyclic dinucleotide was also prepared with a saturated four-carbon linkage using a tandem ring-closing metathesis-hydrogenation procedure. This compound was found to be significantly more stable towards a nucleophilic ring-opening than its unsaturated counterpart. (C) 2004 Elsevier Ltd. All rights reserved.