3',5'-bis-O-[dimethyl(1,1,2-trimethylpropyl)silyl]thymidine | 123533-03-9

• 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',5'-bis-O-[dimethyl(1,1,2-trimethylpropyl)silyl]thymidine
• 英文别名: 3',5'-bis-O-(dimethylthexylsilyl)thymidine；3',5'-bis-O-thexyldimethylsilylthymidine；1-[(2R,4S,5R)-4-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-5-[[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 123533-03-9
• 化学式: C₂₆H₅₀N₂O₅Si₂
• 分子量: 526.864
• InChiKey: KEXLABIQNCPOHS-BHDDXSALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  十二/十四烷基二甲基氧化胺 、 3',5'-bis-O-[dimethyl(1,1,2-trimethylpropyl)silyl]thymidine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到2-(2'-deoxy-3',5'-bis-O-(dimethylthexylsilyl)-β-D-ribofuranosyl)-8-aza-5,8-dimethyl-cis-5,6-diazabicyclo[4.3.0]nonane-2,4-dione
  参考文献：
  名称：

  1,3-DIPOLAR CYCLOADDITION REACTIONS OF 3′,5′-BIS-O-SILYL THYMIDINES. SYNTHESIS OF NOVEL AZABICYCLIC COMPOUNDS

  摘要：

  An efficient one step procedure for the preparation of (4.3.0) bicyclic N-methylpyrrolidine thymidine derivatives 4, using cycloaddition reaction of the highly reactive non-stabilized azomethine ylide [Y] with 3',5'-Bis-O-silylthymidines 3.

  DOI：

  10.1081/scc-120004847
• 作为产物：
  描述：

  二甲基叔己基氯化硅 、 beta-胸苷 生成 3',5'-bis-O-[dimethyl(1,1,2-trimethylpropyl)silyl]thymidine
  参考文献：
  名称：

  MAILLARD, MICHEL;FARAJ, ABDESSLEM;FRAPPIER, FRANCOIS;FLORENT, JEAN-CLAUDE+, TETRAHEDRON LETT., 30,(1989) N5, C. 1955-1958

  摘要：

  DOI：

文献信息

• Synthesis of 3′-substituted-2′,3′-dideoxynucleoside analogs as potential anti-aids drugs
  作者：Michel Maillard、Abdesslem Faraj、François Frappier、Jean-Claude Florent、David S. Grierson、Claude Monneret

  DOI：10.1016/s0040-4039(00)99623-0

  日期：1989.1

  3′-Amino-3′-deoxythymidine was prepared in six steps and in 67% overall yield from thymidine. Five derivatives of and compound were tested for their anti-HIV activity.

  3'-氨基-3'-脱氧胸苷分六个步骤制备，胸腺嘧啶核苷的总收率为67％。五个衍生品和复合他们的抗HIV活性进行了测试。
• Nucleotides, Part LXV, Synthesis of 2′-Deoxyribonucleoside 5′-Phosphoramidites: New Building Blocks for the Inverse (5′-3′)-Oligonucleotide Approach
  作者：Thomas Wagner、Wolfgang Pfleiderer

  DOI：10.1002/1522-2675(20000809)83:8<2023::aid-hlca2023>3.0.co;2-p

  日期：2000.8.9

  The syntheses of the 3'-O-(4,4'-dimethoxytrityl)-protected 5'-phosphoramidites 25-28 and 5'-(hydrogen succinates) 29-32, which can be used as monomeric building blocks for the inverse (5'-3')-oligodeoxyribonucleotide synthesis are described (Scheme). These activated nucleosides and nucleotides were obtained by two slightly different four-step syntheses starting with the base-protected nucleosides 13-20. For the protection of the aglycon residues, the well-established 2-(4-nitrophenyl)ethyl (npe) and [2-(4-nitrophenyl)ethoxy]carbonyl (npeoc) groups were used. The assembly of the oligonucleotides required a slightly increased coupling time of 3 min in application of the common protocol (see Table 1). The use of pyridinium hydrochloride as an activator (instead of 1H-tetrazole) resulted in an extremely shorter activation time of 30 seconds. We established the efficiency of this inverse strategy by the synthesis of the oligonucleotide 3'-conjugates 33 and 34 which carry lipophilic caps derived from cholesterol and vitamin E, respectively, as well as by the formation of (3'-3')- and (5'-5')-internucleotide linkages (see Table 2).
• An Inverse Approach in Oligodeoxyribonucleotide Synthesis
  作者：Thomas Wagner、Wolfgang Pfleiderer

  DOI：10.1080/07328319708006249

  日期：1997.7

  We synthesized 3'-O-dimethoxytrityl-5'O-phosphoramidites and 5'-O-succinates which can be used as monomeric building blocks for the built up of oligodeoxyribonucleotides in the alternative 5'-3' direction. With this inverse strategy oligonucleotide 3'-conjugates as well as 3'-3' and 5'-5' internucleotidic linkages can be easily formed.