bis(trimethylsilyl)-2-thiothymine | 32865-96-6

• 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: bis(trimethylsilyl)-2-thiothymine
• 英文别名: 5-methyl-4-trimethylsilanyloxy-2-trimethylsilanylsulfanyl-pyrimidine；2-S-(trimethylsilyl)-4-O-(trimethylsilyl)thymine；5-Methyl-2-thiouracil-S²,O⁴-bis-(trimethylsilyl)；Trimethyl-(5-methyl-4-trimethylsilyloxypyrimidin-2-yl)sulfanylsilane
• CAS: 32865-96-6
• 化学式: C₁₁H₂₂N₂OSSi₂
• 分子量: 286.545
• InChiKey: YGLNFSXTZCTXPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  326.1±34.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(trimethylsilyl)-2-thiothymine 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 Amberlite IRN-77 resin (H⁺) 、 三正丁基氢锡 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 43.0h， 生成 1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-3-C-trifluoromethyl-β-D-erythropentofuranosyl)-thymine
  参考文献：
  名称：

  3′-Deoxy-3′-C-trifluoromethyl Nucleosides: Synthesis and Antiviral Evaluation

  摘要：

  2',3'-Dideoxy-3'-C-trifluoromethylthymidine 9a and -uridine 9b and 3'-C-trifluoromethyl-d(4)T 11 were prepared in a few steps from 3'-deoxy-3'-C-trifluoromethyl-D-ribose, which synthesis was recently reported. The biological assessment of these nucleoside analogues did not reveal interesting antiviral properties against HIV-1, HSV-1, CMV, Vaccine, and Cox B4.

  DOI：

  10.1080/07328319808004316
• 作为产物：
  描述：

  4-羟基-2-巯基-5-甲基嘧啶 、 N,O-双三甲硅基乙酰胺 以 乙腈 为溶剂， 生成 bis(trimethylsilyl)-2-thiothymine
  参考文献：
  名称：

  A Convenient One-Pot Synthesis of Acyclonucleosides.

  摘要：

  二甲基硅基吡啶碱直接与1,3-二噁烷（或2-甲基-1,3-二噁烷）、氯三甲基硅烷以及金属碘化物（如KI或NaI）在室温下的乙腈中反应，以良好产率合成酰基吡啶衍生物，包括2-硫吡啶衍生物。然而，向2-硫吡啶碱中引入酸性链则需使用2当量的试剂。

  DOI：

  10.1248/cpb.43.142

文献信息

• Compounds and oligomeric compounds comprising novel nucleobases
  申请人：——

  公开号：US20040033973A1

  公开（公告）日：2004-02-19

  The present invention relates to nucleoside compositions comprising novel nucleobases and oligomeric compounds comprising at least one such nucleoside. These oligomeric compounds typically have enhanced binding affinity properties compared to oligomeric compounds without the modification. The oligomeric compounds are useful, for example, for investigative and therapeutic purposes.

  本发明涉及包含新型核碱基的核苷酸组合物以及包含至少一种此类核苷酸的寡聚合物化合物。这些寡聚合物化合物通常具有比没有这种修饰的寡聚合物化合物更强的结合亲和性能。这些寡聚合物化合物可用于调查和治疗等用途。
• Some Aspects on Acyclonucleoside Synthesis
  作者：Masaru Ubasawa、Hideaki Takashima、Kouichi Sdciya

  DOI：10.1080/07328319808004313

  日期：1998.12

  An acyclonucleoside synthesis was investigated on the regioselective introduction of an acyclochain. We found that iodotrimethylsilane catalyzed the reaction of acyclochain introduction as well as its migration from S-2 to N-1 of 2-thiothymine and from N-7 to N-9 position of guanine. By taking the findings into account, several acyclonucleosides were synthesized in a simple one-pot procedure.
• Detailed Studies on Trimethylselyl Triflate Mediated Glycosylation<i>via</i>a 3,5-<i>O</i>-(l,l,3,3-Tetraisopropyl-Disiloxane-l,3-diyl)-2-<i>O</i>-methylribofuranos-l-yl Trichloroacetimidate Intermediate
  作者：Koh-ichiroh Shohda、Takeshi Wada、Mitsuo Sekine

  DOI：10.1080/07328319808004310

  日期：1998.12

  The reaction of 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-methylribofuranos-1-yl trichloroacetimidate as the ribosyl donor with bis(trimethylsilyl)thymine was studied in detail. As the result, it was concluded that the main product is an alpha-glycoside derivative unlike the previous report. In connection with this glycosylation, several chemical properties of the byproduct obtained by the Chapman rearrangement are described.
• A Convenient One-Pot Synthesis of Acyclonucleosides.
  作者：Masaru UBASAWA、Hideaki TAKASHIMA、Kouichi SEKIYA

  DOI：10.1248/cpb.43.142

  日期：——

  Bis(trimethylsilyl)pyrimidine bases were treated directly with 1, 3-dioxolane (or 2-methyl-1, 3-dioxolane), chlorotrimethylsilane and a metal iodide, such as KI or NaI, in acetonitrile at room temperature to afford acylopyrimidine derivatives, including 2-thiopyrimidine derivatives, in good yields. Introduction of an acyclic chain into 2-thiopyrimidine bases, however, necessitated the use of 2 eq of the reagents.

  二甲基硅基吡啶碱直接与1,3-二噁烷（或2-甲基-1,3-二噁烷）、氯三甲基硅烷以及金属碘化物（如KI或NaI）在室温下的乙腈中反应，以良好产率合成酰基吡啶衍生物，包括2-硫吡啶衍生物。然而，向2-硫吡啶碱中引入酸性链则需使用2当量的试剂。
• 3′-Deoxy-3′-<i>C</i>-trifluoromethyl Nucleosides: Synthesis and Antiviral Evaluation
  作者：S. Lavaire、R. Plantier-Royon、C. Portella、M. de Monte、A. Kirn、A.-M. Aubertin

  DOI：10.1080/07328319808004316

  日期：1998.12

  2',3'-Dideoxy-3'-C-trifluoromethylthymidine 9a and -uridine 9b and 3'-C-trifluoromethyl-d(4)T 11 were prepared in a few steps from 3'-deoxy-3'-C-trifluoromethyl-D-ribose, which synthesis was recently reported. The biological assessment of these nucleoside analogues did not reveal interesting antiviral properties against HIV-1, HSV-1, CMV, Vaccine, and Cox B4.