2',5'-dideoxy-5'-(trimethylsilyl)ethynyl-3'-epi-thymidine | 124685-33-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 2',5'-dideoxy-5'-(trimethylsilyl)ethynyl-3'-epi-thymidine
• 英文别名: 1-[(2R,4R,5R)-4-hydroxy-5-(3-trimethylsilylprop-2-ynyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 124685-33-2
• 化学式: C₁₅H₂₂N₂O₄Si
• 分子量: 322.436
• InChiKey: PZXLEBDLMJUQDN-JHJVBQTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  22
• 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：
  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'-(trimethylsilyl)ethynyl-3'-epi-thymidine 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 [(2R,3R,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-prop-2-ynyloxolan-3-yl] methanesulfonate
  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',5'-二-O-甲磺酰基胸苷 在 sodium hydroxide 、 正丁基锂 、 乙醇 、 三氟化硼乙醚 作用下， 生成 2',5'-dideoxy-5'-(trimethylsilyl)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

• The topochemical synthesis of triazole-linked homobasic DNA
  作者：Atchutarao Pathigoolla、Kana M. Sureshan

  DOI：10.1039/c5cc08834h

  日期：——

  Triazolyl-DNA (^TLDNA), DNA wherein phosphodiester units are replaced by triazole units, is of great interest. By adopting Topochemical Azide–Alkyne Cycloaddition (TAAC) reaction, we have synthesized homobasic ^TLDNA oligomers. 5′-ethynyl-3′-azido-2′,3′,5′-tri-deoxycytosine, which crystallized with proximal placement of azide and alkyne units of adjacent molecules, underwent TAAC reaction to ^TLDNA oligomers.

  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。
• Cleavage of a nucleosidic oxetane with carbanions: synthesis of a highly promising candidate for anti-HIV agents — a phosphonate isostere of AZT 5′-phosphate
  作者：Hiromichi Tanaka、Mariko Fukui、Kazuhiro Haraguchi、Mariko Masaki、Tadashi Miyasaka

  DOI：10.1016/s0040-4039(01)80452-4

  日期：1989.1
• 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.
• TANAKA, HIROMICHI;FUKUI, MARIKO;HARAGUCHI, KAZUHIRO;MASAKI, MARIKO;MIYASA+, TETRAHEDRON LETT., 30,(1989) N9, C. 2567-2570
  作者：TANAKA, HIROMICHI、FUKUI, MARIKO、HARAGUCHI, KAZUHIRO、MASAKI, MARIKO、MIYASA+

  DOI：——

  日期：——