2'-deoxy-2'-(4-methoxybenzylthio)uridine | 83088-00-0

• 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: 2'-deoxy-2'-(4-methoxybenzylthio)uridine
• 英文别名: 2'-S-(4-Methoxybenzyl)-2'-thiouridine；2'-deoxy-2'-S-(4-methoxybenzyl)uridine；2'-deoxy-2'-(4-methoxyphenylmethanethio)uridine；1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-[(4-methoxyphenyl)methylsulfanyl]oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 83088-00-0
• 化学式: C₁₇H₂₀N₂O₆S
• 分子量: 380.422
• InChiKey: PDLLPQREXDNEJN-DTZQCDIJSA-N

物化性质

• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2'-deoxy-2'-(4-methoxybenzylthio)uridine 在 吡啶 、 silver nitrate 、 三氟乙酸 、 苯酚 作用下， 以 甲醇 为溶剂， 反应 2.08h， 生成 2'-deoxy-2'-mercaptouridine
  参考文献：
  名称：

  Divakar, K. J.; Mottoh, Alexander; Reese, Colin B., Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 969 - 974

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2'-脱水尿苷 、 4-甲氧基苄硫醇 在 1,1,2,3-四甲基胍 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以80%的产率得到2'-deoxy-2'-(4-methoxybenzylthio)uridine
  参考文献：
  名称：

  Reaction between 2,2′-anhydro-1-β-D-arabinofuranosyluracil and thiolate ions

  摘要：

  DOI：

  10.1039/p19820001625

文献信息

• Synthesis of Nucleosides with 2′-Fixed Lipid Anchors and Their Behavior in Phospholipid Membranes
  作者：Oliver Kaczmarek、Nicolai Brodersen、Andreas Bunge、Ludwig Löser、Daniel Huster、Andreas Herrmann、Anna Arbuzova、Jürgen Liebscher

  DOI：10.1002/ejoc.200701064

  日期：2008.4

  Various new nucleosides bearing one or two lipophilic groups at the 2′-position have been synthesized. The lipophilic substituents were attached to a 2′-hydroxy, 2′-amino, or 2′-thio function. These lipophilic nucleosides anchor in large unilamellar POPC vesicles serving as phospholipid membrane models. The insertion of these molecules into the membranes was investigated by NMR techniques. For comparison

  已经合成了各种在 2' 位带有一个或两个亲脂基团的新核苷。亲脂性取代基连接到 2'-羟基、2'-氨基或 2'-硫代官能团。这些亲脂性核苷锚定在用作磷脂膜模型的大型单层 POPC 囊泡中。通过核磁共振技术研究了这些分子插入到膜中的情况。为了进行比较，还研究了在 2'-、3'-或 5'-位置具有两个或三个亲脂基团的核苷。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008 年）
• Coupling Across a DNA Helical Turn Yields a Hybrid DNA/Organic Catenane Doubly Tailed with Functional Termini
  作者：Yu Liu、Akinori Kuzuya、Ruojie Sha、Johan Guillaume、Risheng Wang、James W. Canary、Nadrian C. Seeman

  DOI：10.1021/ja8041096

  日期：2008.8.1

  We describe the synthesis of a hybrid DNA/organic macrocycle that is prepared by formation of an amide linkage across one full turn of DNA. Formation of a catenane proved that the linkage crossed a turn rather than running along the phosphodiester backbone contour. The product, a doubly tailed catenane, contains 5'- and 3'-termini that can be functionalized further or used to incorporate the catenane structure into other DNA assemblies.
• Fallois, Loic Le Hir de; Decout, Jean-Luc; Fontecave, Marc, Journal of the Chemical Society. Perkin transactions I, 1997, # 17, p. 2587 - 2596
  作者：Fallois, Loic Le Hir de、Decout, Jean-Luc、Fontecave, Marc

  DOI：——

  日期：——
• Nylon/DNA:  Single-Stranded DNA with a Covalently Stitched Nylon Lining
  作者：Lei Zhu、Philip S. Lukeman、James W. Canary、Nadrian C. Seeman

  DOI：10.1021/ja035186r

  日期：2003.8.1

  The synthesis of DNA/nylon ladder oligomers is described. Three stages of the development are addressed: the synthesis of 2'-beta-substituted phosphoramidites, the deprotection/purification protocols of ODNs modified with both amino and carboxyl groups, and amide bond-forming reactions on the ODNs. The established technology and the novel DNA-based ladder oligomer structure opens a pathway to the synthesis of topological molecular objects and networks templated by DNA through versatile DNA nanotechnology. The DNA-based ladder oligomers may find application in the antisense area.