2-amino-9-(3,5-di-O-tert-butyldimethylsilyl-2-deoxy-β-D-ribofuranosyl)-6-(1-propenyl)purine | 188823-59-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-amino-9-(3,5-di-O-tert-butyldimethylsilyl-2-deoxy-β-D-ribofuranosyl)-6-(1-propenyl)purine
• 英文别名: 9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-6-prop-1-enylpurin-2-amine
• CAS: 188823-59-8
• 化学式: C₂₅H₄₅N₅O₃Si₂
• 分子量: 519.835
• InChiKey: WHORBBQUTUASCQ-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  97.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-amino-9-(3,5-di-O-tert-butyldimethylsilyl-2-deoxy-β-D-ribofuranosyl)-6-(1-propenyl)purine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到2-amino-9-(2-deoxy-β-D-ribofuranosyl)-6-(1-propenyl)purine
  参考文献：
  名称：

  2-Aminopurine derivatives with C6-substituted olefin as novel cross-linking agents and the synthesis of the corresponding β-phosphoramidite precursors

  摘要：

  The 6-vinylated 2-aminopurine nucleoside (1), which was prepared by the Pd(0)-catalyzed cross-coupling reaction using guanosine 6-O-tosylate and vinyl-tributylstannane, has been demonstrated as a potential cross-linking agent. However, attempts for its incorporation into oligonucleotides were unsuccessful because of the high reactivity toward nucleophiles. In this study, new 2'-deoxy nucleoside derivatives with 6-(2-substituted vinyl)-2-aminopurine were designed to diminish the reactivity of the vinyl group. These new nucleosides have been shown to maintain reactivity toward potent nucleophiles such as butylamine and thiols, suggesting that they would form cross-linking with the target nucleobase due to the proximity within the sense-antisense duplex. Thus, the corresponding beta-phosphoramidite precursors were successfully prepared, and were applied to an automated oligonucletotide synthesizer. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00069-0
• 作为产物：
  描述：

  3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 三乙胺 、 lithium chloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-amino-9-(3,5-di-O-tert-butyldimethylsilyl-2-deoxy-β-D-ribofuranosyl)-6-(1-propenyl)purine
  参考文献：
  名称：

  2-Aminopurine derivatives with C6-substituted olefin as novel cross-linking agents and the synthesis of the corresponding β-phosphoramidite precursors

  摘要：

  The 6-vinylated 2-aminopurine nucleoside (1), which was prepared by the Pd(0)-catalyzed cross-coupling reaction using guanosine 6-O-tosylate and vinyl-tributylstannane, has been demonstrated as a potential cross-linking agent. However, attempts for its incorporation into oligonucleotides were unsuccessful because of the high reactivity toward nucleophiles. In this study, new 2'-deoxy nucleoside derivatives with 6-(2-substituted vinyl)-2-aminopurine were designed to diminish the reactivity of the vinyl group. These new nucleosides have been shown to maintain reactivity toward potent nucleophiles such as butylamine and thiols, suggesting that they would form cross-linking with the target nucleobase due to the proximity within the sense-antisense duplex. Thus, the corresponding beta-phosphoramidite precursors were successfully prepared, and were applied to an automated oligonucletotide synthesizer. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00069-0

文献信息

• Efficient Synthesis of 6-Substituted Purine Derivatives Using Pd-Catalyzed Cross-Coupling Reactions with 2’-Deoxyguanosine O6-Tosylate
  作者：Fumi Nagatsugi、Yuki Ogata、Shuhei Imoto、Shigeki Sasaki

  DOI：10.3987/com-07-s(u)24

  日期：——

  6-Substituted purine analogs function in a variety of biological activities including antiviral pathways. A number of studies have reported on the development of the efficient synthesis of these nucleoside analogs. We previously demonstrated that oligonucleotides containing 2-amino-6-vinylpurine derivatives react with the cytosine at the target site with extreme selectivity. This was the first finding

  6-取代的嘌呤类似物在包括抗病毒途径在内的多种生物活性中起作用。许多研究报告了这些核苷类似物的有效合成的发展。我们之前证明了含有 2-氨基-6-乙烯基嘌呤衍生物的寡核苷酸与靶位点的胞嘧啶反应具有极高的选择性。这是鸟苷的O 6 -甲苯磺酸酯衍生物作为Pd(0)催化的与乙烯基三丁基锡烷的交叉偶联反应产生2-氨基-6-乙烯基嘌呤的有效底物的第一个发现。为了证明甲苯磺酸盐前体的有用性，在本研究中，我们研究了过渡金属催化剂和配体在使用硼酸或格氏试剂作为偶联伙伴来实现交叉偶联反应中。