2',5'-dideoxy-5'-ethynyl-3'-epi-thymidine | 1048636-94-7

• 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: 2',5'-dideoxy-5'-ethynyl-3'-epi-thymidine
• 英文别名: 1-[(2R,4R,5R)-4-hydroxy-5-prop-2-ynyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1048636-94-7
• 化学式: C₁₂H₁₄N₂O₄
• 分子量: 250.254
• InChiKey: DSZWLZKRCUBFRM-OPRDCNLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2',5'-dideoxy-5'-ethynyl-3'-epi-thymidine 在 吡啶 、 sodium hydroxide 、 乙醇 作用下， 生成 5-methyl-1-[(2R,5R)-5-prop-2-ynyl-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of 5′-Ethynyl-2′-deoxynucleoside Analogues as Building Block for Antisense Oligonucleotide

  摘要：

  New nucleosides and nucleoside analogue dimers were prepared using 5'-ethynyl-2'-deoxynucleoside as starting material.

  DOI：

  10.1080/07328319908044684
• 作为产物：
  描述：

  3',4'-anhydrothymidine 在 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 2',5'-dideoxy-5'-ethynyl-3'-epi-thymidine
  参考文献：
  名称：

  Synthesis of 5′-Ethynyl-2′-deoxynucleoside Analogues as Building Block for Antisense Oligonucleotide

  摘要：

  New nucleosides and nucleoside analogue dimers were prepared using 5'-ethynyl-2'-deoxynucleoside as starting material.

  DOI：

  10.1080/07328319908044684

文献信息

• Electron Mobility in a Mercury-mediated Duplex of Triazole-linked DNA (^TLDNA)
  作者：Hiroyuki Isobe、Naomi Yamazaki、Atsushi Asano、Tomoko Fujino、Waka Nakanishi、Shu Seki

  DOI：10.1246/cl.2011.318

  日期：2011.3.5

  A metal-ion-mediated duplex of triazole-linked DNA (TLDNA) was synthesized via thymine–mercury(II)–thymine (T–Hg–T) base pairing. The electron-transport properties of the mercury-mediated duplex deposited on a solid substrate were determined by time-resolved microwave conductivity (TRMC) measurements.

  通过胸腺嘧啶-汞(II)-胸腺嘧啶(T-Hg-T)碱基配对合成了金属离子介导的三唑连接DNA (TLDNA)双链体。沉积在固体基质上的汞介导双链体的电子传输特性通过时间分辨微波电导率（TRMC）测量来确定。
• Triazole-Linked Analogue of Deoxyribonucleic Acid (^TLDNA): Design, Synthesis, and Double-Strand Formation with Natural DNA
  作者：Hiroyuki Isobe、Tomoko Fujino、Naomi Yamazaki、Marine Guillot-Nieckowski、Eiichi Nakamura

  DOI：10.1021/ol801230k

  日期：2008.9.1

  A new triazole-linked analogue of DNA ((TL)DNA) has been designed and synthesized using click chemistry. The chain elongation reaction using copper-catalyzed Huisgen cycloaddition was successful and gave the artificial oligonucleotide that formed a stable double strand with the complementary strand of natural DNA.
• Convergent synthesis of oligomers of triazole-linked DNA analogue (TLDNA) in solution phase
  作者：Tomoko Fujino、Naomi Yamazaki、Hiroyuki Isobe

  DOI：10.1016/j.tetlet.2009.04.101

  日期：2009.7

  A convergent route for the solution-phase synthesis of oligomeric triazole-linked analogues of DNA ((TL)DNA) has been developed. A one-pot procedure for desilylation of masked acetylene and the ensuing copper-catalyzed Huisgen coupling reaction between oligomers allowed the solution-phase synthesis of 7-mer and 8-mer (TL)DNA in good yield. (C) 2009 Elsevier Ltd. All rights reserved.