5,6-dimethyl-2,4-bis-O-(trimethylsilyl)uracil | 31111-32-7

• 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: 5,6-dimethyl-2,4-bis-O-(trimethylsilyl)uracil
• 英文别名: 5,6-dimethyl-2,4-bis-O-trimethylsilyluracil；4,5-dimethyl-2,6-bis-trimethylsilanyloxy-pyrimidine；2,4-Bis-(trimethylsilyloxy)-5,6-dimethyl-pyrimidin；2,4-Bis-(trimethylsilyloxy)-5,6-dimethylpyrimidin；Pyrimidine, 4,5-dimethyl-2,6-bis(trimethylsiloxy)-；(4,5-dimethyl-6-trimethylsilyloxypyrimidin-2-yl)oxy-trimethylsilane
• CAS: 31111-32-7
• 化学式: C₁₂H₂₄N₂O₂Si₂
• 分子量: 284.506
• InChiKey: RWXWUJZBGRWLRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-dimethyl-2,4-bis-O-(trimethylsilyl)uracil 在 sodium methylate 、 zinc(II) chloride 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 5,6-dimethyl-2'-deoxyuridine
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted and 5,6-Disubstituted 2′-Deoxyuridines

  摘要：

  5-Alkyl(cycloalkyl)-2'-deoxyuridines VIa-VIf were synthesised in high yields by condensation of the corresponding silylated bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform and subsequent deblocking with sodium methoxide in methanol. The beta-configuration, anti-glycosidic conformation and C2'-endo (S) sugar pucker of all of these compounds has been established from their H-1 NMR, C-13 NMR, UV and mass spectra. Under the same conditions, the condensation of silylated 5,6-trimethyleneuracil, resulted in 1:2/alpha:beta anomeric mixture (overall yield 71%) and syn-conformation of the 5,6-trimethylene-2'-deoxyuridine [Xg]. The results of the condensation of the silylated 5,6-dimethyluracil are discussed as well. No significant antiviral activity has been found in testing the synthesised compounds against a range of herpes, influenza and HIV-1 viruses.

  DOI：

  10.1080/15257779408013234
• 作为产物：
  描述：

  5,6-二甲基尿嘧啶 、 三甲基氯硅烷 在 六甲基二硅氮烷 作用下， 生成 5,6-dimethyl-2,4-bis-O-(trimethylsilyl)uracil
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted and 5,6-Disubstituted 2′-Deoxyuridines

  摘要：

  5-Alkyl(cycloalkyl)-2'-deoxyuridines VIa-VIf were synthesised in high yields by condensation of the corresponding silylated bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform and subsequent deblocking with sodium methoxide in methanol. The beta-configuration, anti-glycosidic conformation and C2'-endo (S) sugar pucker of all of these compounds has been established from their H-1 NMR, C-13 NMR, UV and mass spectra. Under the same conditions, the condensation of silylated 5,6-trimethyleneuracil, resulted in 1:2/alpha:beta anomeric mixture (overall yield 71%) and syn-conformation of the 5,6-trimethylene-2'-deoxyuridine [Xg]. The results of the condensation of the silylated 5,6-dimethyluracil are discussed as well. No significant antiviral activity has been found in testing the synthesised compounds against a range of herpes, influenza and HIV-1 viruses.

  DOI：

  10.1080/15257779408013234

文献信息

• SYNTHESIS AND BIOLOGICAL EVALUATION OF ISONUCLEOSIDES DERIVED FROM METHYL 3,5-ANHYDRO-2-<i>O</i>-(2-FLUOROBENZYL)-<scp>d</scp>-XYLOFURANOSIDES
  作者：Jörn Wirsching、Oliver Schulze、Jürgen Voss、Anja Giesler、Jürgen Kopf、Gunadi Adiwidjaja、Jan Balzarini、Erik De Clercq

  DOI：10.1081/ncn-120003290

  日期：2002.4.15

  Abstract New isonucleosides [methyl 5-(1-pyrimidinyl)furanosides] are prepared by nucleophilic opening of the oxetane ring of methyl 3,5-anhydro-2-O-(2-fluorobenzyl)-D-xylofuranoside with silylated pyrimidine bases in the presence of trimethylsilyl triflate. Structures, configurations and conformations were determined by NMR techniques and several X-ray diffraction analyses. seven of the isonucleosides

  摘要 通过甲基 3,5-脱水-2-O-(2-氟苄基)-D-呋喃木糖苷的氧杂环丁烷环与甲硅烷基化嘧啶碱基亲核开环制备了新的异核苷 [甲基 5-(1-嘧啶基)呋喃糖苷]。三氟甲磺酸三甲基甲硅烷基酯的存在。结构、构型和构象通过核磁共振技术和几种 X 射线衍射分析确定。测试了七种异核苷的细胞毒性和对 HIV、HSV 和其他几种病毒的活性。
• THIOSUGARS. VIII.^* PREPARATION OF NEW 4′-THIO-<scp>L</scp>-LYXO PYRIMIDINE NUCLEOSIDE ANALOGUES
  作者：Jörn Wirsching、Jürgen Voss、Gunadi Adiwidjaja、Jan Balzarini、Erik De Clercq

  DOI：10.1081/ncn-100105900

  日期：2001.9.30

  Reaction of 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-L-lyxofuranose with silylated pyrimidine bases and subsequent deprotection with boron tribromide led to 4′-thio-L-lyxo pyrimidine nucleosides. The 5-bromo-6-methyl derivative was prepared from methyl 2,3,5-tri-O-acetyl-4-thio-L-lyxofuranoside. Deacetylation was performed with sodium methoxide. The anomers were separated by HPLC and their configurations

  1-O-乙酰基-2,3,5-tri-O-benzyl-4-thio-L-lyxofuranose 与甲硅烷基化嘧啶碱基反应，随后用三溴化硼脱保护，生成 4'-thio-L-lyxo 嘧啶核苷。5-溴-6-甲基衍生物由甲基 2,3,5-三-O-乙酰-4-硫代-L-lyxofuranoside 制备。用甲醇钠进行脱乙酰。端基异构体通过 HPLC 分离，并通过 NMR 光谱和 X 射线结构分析确定其构型。测试了核苷的生物活性。*第七部分：Wirsching, J.、Voss, J.、Adiwidjaja, G.、Giesler, A.、Kopf, J. Eur。J. 组织 化学 2001 年，印刷中。
• Vorbrueggen, Helmut; Krolikiewicz, Konrad; Bennua, Baerbel, Chemische Berichte, 1981, vol. 114, # 4, p. 1234 - 1255
  作者：Vorbrueggen, Helmut、Krolikiewicz, Konrad、Bennua, Baerbel

  DOI：——

  日期：——
• Synthesis of an AZT-HEPT Hybrid and Homologous AzddU Derivatives.
  作者：Erik Larsen、Krzysztof Danel、Gitte B. Vaaben、Ali A. El-Emam、Erik B. Pedersen、Claus Nielsen、Shu Hai Zhao、Mauro I. Ciglic、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0417

  日期：——

  3'-Azido-2',3'-dideoxyuridines 6 and their corresponding cc anomers 5 were synthesized by condensation of silylated 6-alkyl and 5,6-dialkyl substituted uracils 2 with methyl 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-alpha-beta-D-erythro-pentofuranoside (4). Compounds 5 and 6 were treated with tetrabutylammonium fluoride to obtain the deprotected nucleosides 7 and 8, respectively.
• Synthesis and Antiviral Activity of 1-{[2-(Phenoxy)ethoxy]methyl}uracil Derivatives
  作者：M. S. Novikov、A. A. Ozerov、Yu. A. Orlova、R. W. Buckheit

  DOI：10.1007/s10593-005-0193-5

  日期：2005.5