9-Trimethylsilyl-2-amino-6-chlorpurin | 75788-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-Trimethylsilyl-2-amino-6-chlorpurin
• 英文别名: 6-Chloro-9-(trimethylsilyl)-9H-purin-2-amine；6-chloro-9-trimethylsilylpurin-2-amine
• CAS: 75788-38-4
• 化学式: C₈H₁₂ClN₅Si
• 分子量: 241.755
• InChiKey: VTONZLRMVBZBKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-Trimethylsilyl-2-amino-6-chlorpurin 在 mercaptoethyl alcohol 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 10.0h， 生成 9-[3-deoxy-3-(hydroxymethyl)-β-L-ribofuranosyl]guanine
  参考文献：
  名称：

  L-3'-羟甲基核糖核苷的合成。

  摘要：

  通过关键的中间体碳水化合物8合成目标化合物，该化合物通过首先选择性地保护1'-和2'-羟基，然后选择性地甲苯磺酸化5'-羟基来合成化合物3。然后，制备甲苯磺酰基部分。将其用苄基取代以得到4。化合物4进行Dess-Martin氧化，得到酮5。将化合物5进行Wittig烯化反应，得到烯烃6，然后进行区域选择性氢硼化，得到7。化合物7用乙酸完全乙酰化。 ，乙酸酐和硫酸得到关键中间体8。

  DOI：

  10.1080/15257770008033005
• 作为产物：
  描述：

  六甲基二硅氧烷 、 2-氨基-6-氯嘌呤 在 硫酸氢铵 作用下， 反应 20.0h， 生成 9-Trimethylsilyl-2-amino-6-chlorpurin
  参考文献：
  名称：

  Synthesis of 2′,3′-dideoxy-3′-fluoro-l-ribonucleosides as potential antiviral agents from d-sorbitol

  摘要：

  2',3'-Dideoxy-3'-fluoro-L-ribonucleosides were synthesized as potential antiviral agents. The key intermediate, methyl 5-O-benzoyl-2,3-dideoxy-3-fluoro-L-ribofuranoside, which was prepared from D-sorbitol, was condensed with pyrimidine and purine bases to obtain the respective nucleosides. Among them, the cytosine analogue 2',3'-dideoxy-3'-fluoro-alpha-L-cytidine showed a moderate anti-HBV activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00312-2

文献信息

• Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction
  作者：Chengyuan Liang、Weihui Ju、Shunjun Ding、Han Sun、Gennian Mao

  DOI：10.3390/molecules22010084

  日期：——

  An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently accepted mechanism advanced by Vorbrueggen has been proposed and verified by experiments. In practice, this

  已经开发了在不存在路易斯酸的情况下使用糖基氯化物作为糖基供体的有效的核苷合成方法。糖基氯已被证明是经典的甲硅烷基-希尔伯特-约翰逊反应中的关键中间体。已经提出了一种可能的机制，该机制与Vorbrueggen提出的当前接受的机制不同，并通过实验进行了验证。实际上，这种无催化剂的方法可轻松轻松地获得卡培他滨。
• Asymmetric Synthesis of 2′-<i>C</i>-Methyl-4′-selenonucleosides as Anti-Hepatitis C Virus Agents
  作者：Hyejin Lee、Dnyandev B. Jarhad、Jinha Yu、Choongho Lee、Lak Shin Jeong

  DOI：10.1021/acs.joc.9b01462

  日期：2019.11.15

  anti-hepatitis C virus (HCV) agents, we designed and synthesized the 2'-C-methyl-4'-selenopyrimidine and -purine nucleosides and their phosphoramidate prodrugs to replace a furanose oxygen of anti-HCV nucleos(t)ides with a selenium atom on the basis that selenium is a chemical isostere of oxygen. These nucleosides are expected to show different physicochemical properties such as better lipophilicity which might

  为了寻找抗丙型肝炎病毒（HCV）药物的新模板，我们设计并合成了2'-C-甲基-4'-硒嘧啶和-嘌呤核苷及其氨基磷酸酯前药，以取代抗HCV的呋喃糖氧硒是氧的化学等排体，因此具有硒原子的核苷（t）化物。预计这些核苷将显示出不同的理化性质，例如更好的亲脂性，这可能会增强细胞膜的渗透性以及糖环中大分子硒原子诱导的构象约束。通过2-C-甲基-d-硒代糖的构建，由2-C-甲基-d-核糖体-γ-内酯（14）合成了2'-C-甲基-4'-硒基嘧啶和-嘌呤核苷8和9。图18至C-4差向异构化和SN2环化以及Se2-作为关键步骤。钥匙4' 分别使用Pummerer型重排和Vorbrüggen糖基化将-硒代糖转化为2'-C-甲基-4'-硒代嘧啶和-嘌呤核苷。另外，已经应用ProTide策略来合成腺嘌呤和尿嘧啶氨基磷酸酯衍生物10a和10b，以克服与母体核苷有关的局限性，例如转化为它们相应的5'-单磷酸酯形式的效率低和细胞吸收差。通过2D
• Schmidt, Richard R.; Loesch, Gabriele R.; Fischer, Peter, Chemische Berichte, 1980, vol. 113, # 9, p. 2891 - 2915
  作者：Schmidt, Richard R.、Loesch, Gabriele R.、Fischer, Peter

  DOI：——

  日期：——
• Synthesis of L-3′-Hydroxymethylribonucleosides
  作者：John S. Cooperwood、Vincent Boyd、Giuseppe Gumina、Chung K. Chu

  DOI：10.1080/15257770008033005

  日期：2000.1

  target compounds were synthesized via the key intermediate carbohydrate 8, which was synthesized by first selectively protecting the 1'- and 2'-hydroxyl groups followed by selective tosylation of the 5'-hydroxyl group to obtain compound 3. The tosyl moiety was then replaced by a benzyl either to obtain 4. Compound 4 underwent Dess-Martin oxidation to afford the ketone 5. Compound 5 was subjected to Wittig

  通过关键的中间体碳水化合物8合成目标化合物，该化合物通过首先选择性地保护1'-和2'-羟基，然后选择性地甲苯磺酸化5'-羟基来合成化合物3。然后，制备甲苯磺酰基部分。将其用苄基取代以得到4。化合物4进行Dess-Martin氧化，得到酮5。将化合物5进行Wittig烯化反应，得到烯烃6，然后进行区域选择性氢硼化，得到7。化合物7用乙酸完全乙酰化。 ，乙酸酐和硫酸得到关键中间体8。
• Synthesis of 2′,3′-dideoxy-3′-fluoro-l-ribonucleosides as potential antiviral agents from d-sorbitol
  作者：Byoung K Chun、Raymond F Schinazi、Yung-Chi Cheng、Chung K Chu

  DOI：10.1016/s0008-6215(99)00312-2

  日期：2000.8

  2',3'-Dideoxy-3'-fluoro-L-ribonucleosides were synthesized as potential antiviral agents. The key intermediate, methyl 5-O-benzoyl-2,3-dideoxy-3-fluoro-L-ribofuranoside, which was prepared from D-sorbitol, was condensed with pyrimidine and purine bases to obtain the respective nucleosides. Among them, the cytosine analogue 2',3'-dideoxy-3'-fluoro-alpha-L-cytidine showed a moderate anti-HBV activity. (C) 2000 Elsevier Science Ltd. All rights reserved.