苯酰胺,N-(三甲基甲硅烷基)-N-[7-(三甲基甲硅烷基)-7H-嘌呤-6-基]- | 18055-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 苯酰胺,N-(三甲基甲硅烷基)-N-[7-(三甲基甲硅烷基)-7H-嘌呤-6-基]-
• 英文名称: N-trimethylsilanyl-N-(7-trimethylsilanyl-7H-purin-6-yl)-benzamide
• 英文别名: N-trimethylsilyl-N-(7-trimethylsilylpurin-6-yl)benzamide
• CAS: 18055-46-4
• 化学式: C₁₈H₂₅N₅OSi₂
• 分子量: 383.6
• InChiKey: OVOMEWZVOPHWGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯酰胺,N-(三甲基甲硅烷基)-N-[7-(三甲基甲硅烷基)-7H-嘌呤-6-基]- 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 四氯化锡 、 一水合肼 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 生成
  参考文献：
  名称：

  Synthesis and antiviral activity of 3′-C-branched-3′-deoxy analogues of adenosine

  摘要：

  The synthesis of some 3'-C-branched-3'-deoxy adenine nucleosides is described, Starting from the known 3-deoxy-3-C-(hydroxymethyl)-1,2;5,6-di-O-isopropylidene-alpha-D-allofuranose (1), a versatile glycosylating agent, namely 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-C-(mesyloxymethyl)-beta-D-ribofuranose (6), was prepared in three steps, Condensation of the latter with bis(trimethysilylated) N-6-benzoyladenine in the presence of tin(IV) chloride gave the N-9-beta-nucleoside 7. Compound 7 was converted into (i) 9-[3-C-(azidomethyl)-3-deoxy-beta-D-ribofuranosyl]adenine (10), (ii) 9-[3-C-(azidomethyl)-2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl]adenine (14) and 9-[2-azido-3-C-(azidomethyl)-2,3-dideoxy-beta-D-arabinofuranosyl]adenine (15), and (iii) 9-[3-deoxy-2-O,3-C-(methylene)-beta-D-ribofuranosyl]adenine (16). None of the tested nucleosides showed marked cytostatic or antiviral activity in vitro. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0008-6215(96)00028-6
• 作为试剂：
  描述：

  [(2S,4R,5S)-4,5-diacetyloxyoxolan-2-yl]methyl 2,2-dimethylpropanoate 、 苯酰胺,N-(三甲基甲硅烷基)-N-[7-(三甲基甲硅烷基)-7H-嘌呤-6-基]- 在 苯酰胺,N-(三甲基甲硅烷基)-N-[7-(三甲基甲硅烷基)-7H-嘌呤-6-基]- 作用下， 以65的产率得到[(2S,4R,5R)-4-acetyloxy-5-(6-benzamidopurin-9-yl)oxolan-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  J. Am. Chem. Soc. 1996, 118, 6648-6659

  摘要：

  DOI：

文献信息

• Preparation of 2-(3-Hydroxyalkylthio)benzoxazoles and their Conversion into Thietanes
  作者：Dai Ikemizu、Ayako Matsuyama、Kazunori Takemura、Oyo Mitsunobu

  DOI：10.1055/s-1997-1032

  日期：1997.11

  Reaction of primary or secondary 1,3-diols with dibenzoxazol-2-yl disulfide and tributylphosphine or triphenylphosphine selectively gave 2-(3-hydroxyalkylthio)benzoxazoles which, on treatment with KH, were converted into the corresponding thietanes. 2,2-Dibenzylthietane-1-oxide reacted with silylated purines and pyrimidines in the presence of TMSOTf and ZnI2 to give the corresponding thietane nucleosides in 17-69% yields.

  初级或次级1,3-二醇与二苯并噻唑-2-基二硫和三丁基磷或三苯基磷的反应选择性地生成2-(3-羟基烷基硫)苯并噻唑，在与氢化钾处理后转化为相应的硫杂环己烷。2,2-二苯基硫杂环己烷-1-氧化物在TMSOTf和ZnI2的存在下与硅化嘌呤和嘧啶反应，得到相应的硫杂环核苷，收率为17-69%。
• Angew. Chem. Int. Ed. Engl. 1995, 34, 350-352
  作者：

  DOI：——

  日期：——
• Synthesis and antiviral activity of 3′-C-branched-3′-deoxy analogues of adenosine
  作者：I Mikhailopulo

  DOI：10.1016/0008-6215(96)00028-6

  日期：1996.5.14

  The synthesis of some 3'-C-branched-3'-deoxy adenine nucleosides is described, Starting from the known 3-deoxy-3-C-(hydroxymethyl)-1,2;5,6-di-O-isopropylidene-alpha-D-allofuranose (1), a versatile glycosylating agent, namely 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-C-(mesyloxymethyl)-beta-D-ribofuranose (6), was prepared in three steps, Condensation of the latter with bis(trimethysilylated) N-6-benzoyladenine in the presence of tin(IV) chloride gave the N-9-beta-nucleoside 7. Compound 7 was converted into (i) 9-[3-C-(azidomethyl)-3-deoxy-beta-D-ribofuranosyl]adenine (10), (ii) 9-[3-C-(azidomethyl)-2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl]adenine (14) and 9-[2-azido-3-C-(azidomethyl)-2,3-dideoxy-beta-D-arabinofuranosyl]adenine (15), and (iii) 9-[3-deoxy-2-O,3-C-(methylene)-beta-D-ribofuranosyl]adenine (16). None of the tested nucleosides showed marked cytostatic or antiviral activity in vitro. (C) 1996 Elsevier Science Ltd.
• J. Am. Chem. Soc. 1996, 118, 6648-6659
  作者：

  DOI：——

  日期：——