N'-[9-((2R,4S,5R)-5-Aminomethyl-4-hydroxy-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-N,N-dibutyl-formamidine | 669083-49-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: N'-[9-((2R,4S,5R)-5-Aminomethyl-4-hydroxy-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-N,N-dibutyl-formamidine
• 英文别名: 5'-Amino-2',5'-dideoxy-N-[(dibutylamino)methylidene]guanosine；N'-[9-[(2R,4S,5R)-5-(aminomethyl)-4-hydroxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-N,N-dibutylmethanimidamide
• CAS: 669083-49-2
• 化学式: C₁₉H₃₁N₇O₃
• 分子量: 405.5
• InChiKey: RWVHPSYSLWPVKA-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N'-[9-((2R,4S,5R)-5-Aminomethyl-4-hydroxy-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-N,N-dibutyl-formamidine 在 4-二甲氨基吡啶 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 7.0h， 生成 Diisopropyl-phosphoramidous acid 2-cyano-ethyl ester (2R,3S,5R)-5-[2-(dibutylamino-methyleneamino)-6-oxo-1,6-dihydro-purin-9-yl]-2-({[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-methyl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of a formamidine-protected 5′-amino-2′,5′-dideoxyguanosine phosphoramidite and preparation of 5′-acylamidooligonucleotides

  摘要：

  A 5'-amino-2',5'-dideoxyguanosine phosphoramidite building block for DNA synthesis was prepared from 2-N-(dibutylformamidino)-2'-deoxyguanosine in four steps and 68% overall yield. Two of the three steps of the conversion from the 5'-alcohol to the monomethoxytritylamine were performed in the same flask. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.003
• 作为产物：
  描述：

  2-N-((di-n-butylamino)methylene)-2'-deoxyguanosine 在 偶氮二甲酸二异丙酯 、 乙二胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 N'-[9-((2R,4S,5R)-5-Aminomethyl-4-hydroxy-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-N,N-dibutyl-formamidine
  参考文献：
  名称：

  Synthesis of a formamidine-protected 5′-amino-2′,5′-dideoxyguanosine phosphoramidite and preparation of 5′-acylamidooligonucleotides

  摘要：

  A 5'-amino-2',5'-dideoxyguanosine phosphoramidite building block for DNA synthesis was prepared from 2-N-(dibutylformamidino)-2'-deoxyguanosine in four steps and 68% overall yield. Two of the three steps of the conversion from the 5'-alcohol to the monomethoxytritylamine were performed in the same flask. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.003

文献信息

• Synthesis of a formamidine-protected 5′-amino-2′,5′-dideoxyguanosine phosphoramidite and preparation of 5′-acylamidooligonucleotides
  作者：Jan A. Rojas Stütz、Clemens Richert

  DOI：10.1016/j.tetlet.2003.11.003

  日期：2004.1

  A 5'-amino-2',5'-dideoxyguanosine phosphoramidite building block for DNA synthesis was prepared from 2-N-(dibutylformamidino)-2'-deoxyguanosine in four steps and 68% overall yield. Two of the three steps of the conversion from the 5'-alcohol to the monomethoxytritylamine were performed in the same flask. (C) 2003 Elsevier Ltd. All rights reserved.