N2-二甲基甲脒-2'-甲氧基鸟苷 | 183737-04-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: N2-二甲基甲脒-2'-甲氧基鸟苷
• 英文名称: N2-dimethylaminomethylene-2'-O-methylguanosine
• 英文别名: N2-Dimethylformamidine-2'-O-methyl-guanosine；N'-[9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-N,N-dimethylmethanimidamide
• CAS: 183737-04-4
• 化学式: C₁₄H₂₀N₆O₅
• 分子量: 352.35
• InChiKey: KDQQTCFKBCWYFL-QYVSTXNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N2-二甲基甲脒-2'-甲氧基鸟苷 在 吡啶 、 咪唑 、 ammonium hydroxide 、 sodium cyanoborohydride 、 三苯基膦 、 甲基肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.5h， 生成 N-(9-{(2R,3R,4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-5-[(N-methyl-aminooxy)-methyl]-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-isobutyramide
  参考文献：
  名称：

  An Efficient Multigram Synthesis of Monomers for the Preparation of Novel Oligonucleotides Containing Isosteric Non-Phosphorous Backbones

  摘要：

  The facile preparation of two novel classes of nucleoside analogs for the inclusion as dimeric non-phosphorous containing subunits in chimeric backbones has been accomplished. The concise preparation of 3'-formylnucleosides and 5'-O-(N-methylhydroxylamino)-nucleosides is reported.

  DOI：

  10.1080/07328319708006242
• 作为产物：
  描述：

  N'-[9-[(4aR,6R,7R,7aR)-2,2-ditert-butyl-7-methoxy-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl]-6-oxo-1H-purin-2-yl]-N,N-dimethylmethanimidamide 在 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以0.107 g的产率得到N2-二甲基甲脒-2'-甲氧基鸟苷
  参考文献：
  名称：

  Facile and efficient approach for the synthesis of N2-dimethylaminomethylene-2′-O-methylguanosine

  摘要：

  A convenient method for the synthesis of N-2-dimethylaminomethylene-2'-O-methylguanosine (1), which is a useful intermediate for oligonucleotide construction, was developed. We chose the di-tert-butylsilyl group and the triisopropylbenzenesulfonyl group as sugar and base protecting groups, respectively. These protecting groups were stable during the 2'-O-methylation step with MeI and NaH. Our six-step synthesis of 1 is easy to perform using commercially available reagents, and requires only three chromatographic purifications. Compound 1 was obtained in 56% yield from guanosine. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.016

文献信息

• Synthesis of Novel Nucleic Acid Mimics <i>via</i> the Stereoselective Intermolecular Radical Coupling of 3‘-Iodo Nucleosides and Formaldoximes¹
  作者：Balkrishen Bhat、Eric E. Swayze、Patrick Wheeler、Stuart Dimock、Michel Perbost、Yogesh S. Sanghvi

  DOI：10.1021/jo961549c

  日期：1996.11.15

  5-methylcytosine) and purine (adenine, guanine) bases. The reaction was highly stereoselective, giving only a single dimeric species having the ribo-configuration of the newly introduced C-3'-branched methylene moiety. Also prepared were dimers 16, incorporating 2'-O-methyl ribonucleosides in both halves of the dimer. This required the synthesis of 3'-deoxy-3'-iodo-2'-O-methyl nucleosides 12 as well as 2'-O-me

  由双（三甲基锡烷基）苯并频哪酸酯（8）介导的烷基碘和肟的高度收敛性自由基偶联已被用于制备一系列二聚核苷，以模拟天然核酸。反应条件的系统优化允许将适当的碘化物和肟单步转化为中等至极好的收率的2'-脱氧二聚体9。例如，3'-脱氧-3'-碘-5'-（三苯基甲基）胸苷（6a）与3'-O-（叔丁基二苯基甲硅烷基）-5'-O-（亚甲基亚氨基）胸苷（7a）的反应在8存在下，在脱气的苯中得到81％的3'-脱（氧膦）-3'-（亚甲基亚氨基）-5'-O-（三苯甲基）胸苷基-（3'-> 5'）-3 -O-（叔丁基二苯基甲硅烷基）胸苷（9a）。同样制备的是含有嘧啶（胸腺嘧啶，5-甲基胞嘧啶）和嘌呤（腺嘌呤，鸟嘌呤）碱基的二聚体。该反应是高度立体选择性的，仅给出具有新引入的C-3'-支链亚甲基部分的核糖构型的单个二聚体物质。还制备了二聚体16，在二聚体的两半中都掺入了2'-O-甲基核糖核苷。这需要合成3'-脱氧-3
• Groetli, Morten; Douglas, Mark; Beijer, Barbro, Journal of the Chemical Society. Perkin transactions I, 1997, # 18, p. 2779 - 2788
  作者：Groetli, Morten、Douglas, Mark、Beijer, Barbro、Garcia, Ramon Gueimil、Eritja, Ramon、Sproat, Brian

  DOI：——

  日期：——