1-((2R,4S,5R)-5-((5-((((3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dipentadecyltetrahydrofuro-[3,4-d][1,3]dioxol-4-yl)methoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione | 1449569-69-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 1-((2R,4S,5R)-5-((5-((((3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dipentadecyltetrahydrofuro-[3,4-d][1,3]dioxol-4-yl)methoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS: 1449569-69-0
• 化学式: C₅₃H₈₇N₇O₁₀
• 分子量: 982.315
• InChiKey: YQRCVZCUCFQFEE-DZKYYITRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.19
• 重原子数：
  70.0
• 可旋转键数：
  36.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  206.81
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  1-((2R,4S,5R)-5-((5-((((3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dipentadecyltetrahydrofuro-[3,4-d][1,3]dioxol-4-yl)methoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以54.4%的产率得到2-cyanoethyl (2R,3S,5R)-2-((5-((((3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dipentadecyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)-methyl)-1H-1,2,3-triazol-1-yl)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl diisopropylphosphoramidite
  参考文献：
  名称：

  Quantum Dot Lipid Oligonucleotide Bioconjugates: Toward a New Anti-MicroRNA Nanoplatform

  摘要：

  The construction of new nanotools is presented here using the example of fluorescent semiconductor nanocrystals, quantum dots (QDs). In this study, the implementation of the new lipid oligonucleotide conjugate-functionalized quantum dots (LON-QDs) is realized in four steps: (i) the synthesis of the lipid oligonudeotide conjugates (LONs), (ii) the encapsulation of QDs by nucleolipids and LONs, (iii) the study of the duplex formation of LON-QDs with the complementary ON partners, and (iv) the cellular uptake of the LON-QD platform and hybridization with the target ONs (microRNA and miR-21).

  DOI：

  10.1021/bc400157z
• 作为产物：
  描述：

  1-(6-hydroxymethyl-2,2-dipentadecyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidin-2,4-dione 在 sodium hydride 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 34.0h， 生成 1-((2R,4S,5R)-5-((5-((((3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dipentadecyltetrahydrofuro-[3,4-d][1,3]dioxol-4-yl)methoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Quantum Dot Lipid Oligonucleotide Bioconjugates: Toward a New Anti-MicroRNA Nanoplatform

  摘要：

  The construction of new nanotools is presented here using the example of fluorescent semiconductor nanocrystals, quantum dots (QDs). In this study, the implementation of the new lipid oligonucleotide conjugate-functionalized quantum dots (LON-QDs) is realized in four steps: (i) the synthesis of the lipid oligonudeotide conjugates (LONs), (ii) the encapsulation of QDs by nucleolipids and LONs, (iii) the study of the duplex formation of LON-QDs with the complementary ON partners, and (iv) the cellular uptake of the LON-QD platform and hybridization with the target ONs (microRNA and miR-21).

  DOI：

  10.1021/bc400157z