2'-O-methyl-5'-deoxy-5'-thiouridine | 174088-75-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 2'-O-methyl-5'-deoxy-5'-thiouridine
• 英文别名: 1-[(2R,3R,4S,5S)-4-hydroxy-3-methoxy-5-(sulfanylmethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 174088-75-6
• 化学式: C₁₀H₁₄N₂O₅S
• 分子量: 274.298
• InChiKey: MHJLKDYYMNCGGM-ZOQUXTDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  89.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-O-methyl-5'-deoxy-5'-thiouridine 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Synthesis of 2′-Substituted Sulfide-Linked Dinucleotides

  摘要：

  3'-Deoxy-3'-(2-mesyloxyethyl)ribofuranosylthymine derivative 3, and its 2'-methoxy (16) and 2'-deoxy (38) analogs were condensed with 5'-deoxy-5'-thiothymidine 4 and 17 or 2'-O-methyl-5'-deoxy-5'-thiouridine 34 and 37 to provide, after standard functional group transformations, thymidine-thymidine and uridine-thymidine dimers 9, 21, 43 and 47. Oxidation of model sulfide dimer 48 with oxone gave sulfone 49. It was not stable to 27% ammonia.

  DOI：

  10.1080/15257779508010717
• 作为产物：
  描述：

  3',5'-O-(1,1,3,3-四异丙基-1,3-二硅氧烷)尿苷 在 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 氨 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.42h， 生成 2'-O-methyl-5'-deoxy-5'-thiouridine
  参考文献：
  名称：

  Synthesis of 2′-Substituted Sulfide-Linked Dinucleotides

  摘要：

  3'-Deoxy-3'-(2-mesyloxyethyl)ribofuranosylthymine derivative 3, and its 2'-methoxy (16) and 2'-deoxy (38) analogs were condensed with 5'-deoxy-5'-thiothymidine 4 and 17 or 2'-O-methyl-5'-deoxy-5'-thiouridine 34 and 37 to provide, after standard functional group transformations, thymidine-thymidine and uridine-thymidine dimers 9, 21, 43 and 47. Oxidation of model sulfide dimer 48 with oxone gave sulfone 49. It was not stable to 27% ammonia.

  DOI：

  10.1080/15257779508010717

文献信息

• Enzymatic nucleic acids containing 5'-and/or 3'-cap structures
  申请人：Matulic-Adamic Jasenka

  公开号：US20050074760A1

  公开（公告）日：2005-04-07

  An enzymatic nucleic acid molecule comprising a 5′- and/or a 3′-cap structure, wherein said structure is not a 5′-5′-linked inverted nucleotide or a 3′-3′-linked inverted nucleotide.

  一种酶性核酸分子，包括5'-和/或3'-端帽结构，其中所述结构不是5'-5'-连接的反向核苷酸或3'-3'-连接的反向核苷酸。
• Synthesis of methoxy nucleosides and enzymatic nucleic acid molecules
  申请人：RIBOZYME PHARMACEUTICALS, INC.

  公开号：EP1108724A2

  公开（公告）日：2001-06-20

  This invention relates to chemical synthesis of 2'-O-methyl, 3'-O-methyl and 5'-O-methyl nucleosides, incorporation of novel chemical modifications in enzymatic nucleic acid molecules and improved methods for the synthesis of enzymatic nucleic acid molecules.

  本发明涉及 2'-O-甲基、3'-O-甲基和 5'-O-甲基核苷的化学合成、在酶核酸分子中加入新型化学修饰以及改进酶核酸分子的合成方法。
• US5998203A
  申请人：——

  公开号：US5998203A

  公开（公告）日：1999-12-07
• US6586238B1
  申请人：——

  公开号：US6586238B1

  公开（公告）日：2003-07-01
• Synthesis of 2′-Substituted Sulfide-Linked Dinucleotides
  作者：Daguang Wang、Bin Meng、Masad J. Damha、George Just

  DOI：10.1080/15257779508010717

  日期：1995.11

  3'-Deoxy-3'-(2-mesyloxyethyl)ribofuranosylthymine derivative 3, and its 2'-methoxy (16) and 2'-deoxy (38) analogs were condensed with 5'-deoxy-5'-thiothymidine 4 and 17 or 2'-O-methyl-5'-deoxy-5'-thiouridine 34 and 37 to provide, after standard functional group transformations, thymidine-thymidine and uridine-thymidine dimers 9, 21, 43 and 47. Oxidation of model sulfide dimer 48 with oxone gave sulfone 49. It was not stable to 27% ammonia.