3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynylthymidine | 945971-35-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynylthymidine
• 英文别名: 1-[(2R,4S,5R)-4-azido-5-(3-trimethylsilylprop-2-ynyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 945971-35-7
• 化学式: C₁₅H₂₁N₅O₃Si
• 分子量: 347.449
• InChiKey: JVSSYYUQKVDCPC-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynylthymidine 在 甲醇 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以97%的产率得到9-(3'-azido-5'-ethynyl-2',3',5'-trideoxy-β-D-ribofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (TLDNA)

  摘要：

  Deoxyribonucleoside analogues bearing acetylene group at the pseudo-5'-position and azido group at the pseudo-3'-position have been synthesized by transglycosylation reaction of deoxythymidine analogue with adenine, cytosine, and guanine nucleobases as nucleophiles. The structures of analogues were studied in crystalline state by X-ray crystallography as well as in solution phase by NMR spectroscopy and showed the puckering conformations similar to the natural congeners. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.046
• 作为产物：
  描述：

  2',5'-dideoxy-5'-(trimethylsilyl)ethynyl-3'-epi-thymidine 在 吡啶 、 甲基磺酰氯 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynylthymidine
  参考文献：
  名称：

  The topochemical synthesis of triazole-linked homobasic DNA

  摘要：

  Triazolyl-DNA（TLDNA），其中磷酸二酯单元被三唑单元取代，具有极大的兴趣。通过采用拓扑化学叠氮-炔烃环加成（TAAC）反应，我们合成了同源的TLDNA寡聚体。5'-乙炔基-3'-叠氮基-2'，3'，5'-三去氧胞嘧啶，与相邻分子的叠氮和炔烃单元靠近结晶，经历了TAAC反应形成TLDNA寡聚体。

  DOI：

  10.1039/c5cc08834h

文献信息

• Triazole-Linked DNA as a Primer Surrogate in the Synthesis of First-Strand cDNA
  作者：Tomoko Fujino、Ken-ichi Yasumoto、Naomi Yamazaki、Ai Hasome、Kazuhiro Sogawa、Hiroyuki Isobe

  DOI：10.1002/asia.201100712

  日期：2011.11.4

  A phosphate‐eliminated nonnatural oligonucleotide serves as a primer surrogate in reverse transcription reaction of mRNA. Despite of the nonnatural triazole linkages in the surrogate, the reverse transcriptase effectively elongated cDNA sequences on the 3′‐downstream of the primer by transcription of the complementary sequence of mRNA. A structure–activity comparison with the reference natural oligonucleotides

  磷酸消除的非天然寡核苷酸可作为mRNA逆转录反应中的引物替代物。尽管在替代物中存在非天然三唑键，但逆转录酶通过转录mRNA的互补序列有效地延长了引物3'下游的cDNA序列。与参考天然寡核苷酸的结构活性比较表明，含有三唑键的替代物具有更好的引发活性。非天然连接还可以保护转录的cDNA免于与5'-核酸外切酶的消化反应，并使我们能够去除未知来源的噪音转录本。
• Synthesis of Triazole-linked Homonucleoside Polymers through Topochemical Azide-Alkyne Cycloaddition
  作者：Atchutarao Pathigoolla、Kana M. Sureshan

  DOI：10.1002/anie.201404797

  日期：2014.9.1

  conventional solution or solid‐phase DNA synthesis is limited for making DNA analogues with unnatural linkages. Other limitations associated with conventional synthesis include difficulty in making larger polymers, poor yield, incomplete reaction, and difficult purification. To circumvent these problems, a single‐crystal‐to‐single‐crystal (SCSC) synthesis of a 1,5‐triazole‐linked polymeric ssDNA analogue from

  开发用于各种领域的稳定的修饰核酸引起了极大的兴趣。磷酸修饰的DNA类似物（其中磷酸二酯基被替代基团取代）具有吸引力，因为它们具有很高的稳定性和对核酸酶的抵抗力。但是，常规溶液或固相DNA合成的范围仅限于制备具有非天然连接的DNA类似物。与常规合成相关的其他限制包括难以制备更大的聚合物，收率低，反应不完全和纯化困难。为了解决这些问题，据报道，通过拓扑化学的叠氮化物-炔烃环加成反应（TAAC），从修饰的核苷中合成了1,5-三唑连接的聚合物ssDNA类似物的单晶对单晶（SCSC）。这是第一款无溶剂的产品，
• 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.
• Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (TLDNA)
  作者：Tomoko Fujino、Nobuhide Tsunaka、Marine Guillot-Nieckowski、Waka Nakanishi、Takeaki Iwamoto、Eiichi Nakamura、Hiroyuki Isobe

  DOI：10.1016/j.tetlet.2010.02.046

  日期：2010.4

  Deoxyribonucleoside analogues bearing acetylene group at the pseudo-5'-position and azido group at the pseudo-3'-position have been synthesized by transglycosylation reaction of deoxythymidine analogue with adenine, cytosine, and guanine nucleobases as nucleophiles. The structures of analogues were studied in crystalline state by X-ray crystallography as well as in solution phase by NMR spectroscopy and showed the puckering conformations similar to the natural congeners. (C) 2010 Elsevier Ltd. All rights reserved.