8-(N-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N²-dimethoxytrityl-2'-deoxyguanosine | 479408-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 8-(N-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N²-dimethoxytrityl-2'-deoxyguanosine
• 英文别名: 2-N-[bis(4-methoxyphenyl)-phenylmethyl]-9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-8-N-(9H-fluoren-2-yl)-6-phenylmethoxypurine-2,8-diamine
• CAS: 479408-24-7
• 化学式: C₆₃H₇₄N₆O₆Si₂
• 分子量: 1067.49
• InChiKey: JXJRARKLNSZYSA-SQTUBTBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.84
• 重原子数：
  77
• 可旋转键数：
  20
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  8-(N-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N²-dimethoxytrityl-2'-deoxyguanosine 在 盐酸 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 5.0h， 生成 8-(N-acetyl-2-amino-fluorene)-O6-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N2-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine
  参考文献：
  名称：

  Preparation of C8-Amine and Acetylamine Adducts of 2‘-Deoxyguanosine Suitably Protected for DNA Synthesis

  摘要：

  C8-Amine and acetylamine adducts of 2'-deoxyguanosine were synthesized. Our approach provides solutions for the coupling of aromatic amines to a protected 8-bromo-2'-deoxyguanosine derivative, for the selective acetylation of the coupled adduct at N-8 and for a protecting group scheme preserving the integrity of the base-labile N-8 acetyl group during DNA synthesis.

  DOI：

  10.1021/ol026474f
• 作为产物：
  描述：

  3',5'-O,O'-bis(tert-butyldimethylsilyl)-8-bromo-2'-deoxyguanosine 在 吡啶 、 tris(dibenzylideneacetone)dipalladium (0) 、 偶氮二甲酸二异丙酯 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三苯基膦 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 5.0h， 生成 8-(N-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N²-dimethoxytrityl-2'-deoxyguanosine
  参考文献：
  名称：

  Preparation of C8-Amine and Acetylamine Adducts of 2‘-Deoxyguanosine Suitably Protected for DNA Synthesis

  摘要：

  C8-Amine and acetylamine adducts of 2'-deoxyguanosine were synthesized. Our approach provides solutions for the coupling of aromatic amines to a protected 8-bromo-2'-deoxyguanosine derivative, for the selective acetylation of the coupled adduct at N-8 and for a protecting group scheme preserving the integrity of the base-labile N-8 acetyl group during DNA synthesis.

  DOI：

  10.1021/ol026474f

文献信息

• A practical approach for the chemical synthesis of 2′-deoxyguanosine-C8 adducts with mutagenic/carcinogenic amino- or nitro-arenes
  作者：Takeji Takamura-Enya、Satoko Ishikawa、Masataka Mochizuki、Keiji Wakabayashi

  DOI：10.1016/s0040-4039(03)01484-9

  日期：2003.8

  of 2′-deoxyguanosine-C8 (dG-C8) adducts with several mutagenic and carcinogenic amino- or nitro-arenes were developed using the palladium-mediated cross-coupling reaction of protected 8-amino-dG with bromoarenes in around 80% yields, followed by conventional deprotection procedures. This approach can be applied to preparation of a variety of authentic dG-C8 adducts with amino or nitro-arenes.

  利用钯介导的受保护的8-氨基-dG与溴代芳烃的交叉偶联反应，开发了合成具有几种致突变和致癌的氨基或硝基芳烃的2'-脱氧鸟苷-C8（dG-C8）加合物的合成方法。大约80％的收率，然后进行常规的脱保护程序。该方法可用于制备各种带有氨基或硝基芳烃的可靠的dG-C8加合物。
• Chemical Synthesis of 2‘-Deoxyguanosine−C8 Adducts with Heterocyclic Amines:  An Application to Synthesis of Oligonucleotides Site-Specifically Adducted with 2-Amino-1-methyl-6-phenylimidazo[4,5-<i>b</i>]pyridine
  作者：Takeji Takamura-Enya、Satoko Ishikawa、Masataka Mochizuki、Keiji Wakabayashi

  DOI：10.1021/tx050296s

  日期：2006.6.1

  Synthesis of 2'-deoxyguanosine-C8 adducts (dG-C8 adducts) with mutagenic/carcinogenic heterocyclic amines (HCAs) was achieved via the Buchwald-Hartwig arylamination reaction. By using tris(dibenzylideneacetone)dipalladium (Pd(2)dba(3)) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (xantphos) with a cesium carbonate (Cs(2)CO(3)) base at a reaction temperature of 100 approximately 120 degrees C

  通过诱变/致癌杂环胺（HCA）合成2'-脱氧鸟苷-C8加合物（dG-C8加合物）是通过Buchwald-Hartwig芳基化反应完成的。通过使用三（二亚苄基丙酮）二钯（Pd（2）dba（3））和9,9-二甲基-4,5-双（二苯基膦基）氧杂蒽（xantphos）与碳酸铯（Cs（2）CO（3））在100的大约120摄氏度的反应温度下，我们获得了dG-C8加合物与2-氨基-3-甲基咪唑并[4,5-f]喹啉（IQ），2-氨基-6-甲基联吡啶[1]的衍生物， 2-a：3'，2'-d]咪唑（Glu-P-1），3-氨基-1,4-二甲基-5H-吡啶并[4,3-b]吲哚（Trp-P-1），约69％的2-氨基-3,8-二甲基咪唑并[4,5-f]喹喔啉（MeIQx）和2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶（PhIP） 8-溴脱氧鸟嘌呤衍生物的交叉偶联得到的收率。如果是PhIP，发现二甲基亚砜（DM
• Preparation of C8-Amine and Acetylamine Adducts of 2‘-Deoxyguanosine Suitably Protected for DNA Synthesis
  作者：Ludovic C. J. Gillet、Orlando D. Schärer

  DOI：10.1021/ol026474f

  日期：2002.11.1

  C8-Amine and acetylamine adducts of 2'-deoxyguanosine were synthesized. Our approach provides solutions for the coupling of aromatic amines to a protected 8-bromo-2'-deoxyguanosine derivative, for the selective acetylation of the coupled adduct at N-8 and for a protecting group scheme preserving the integrity of the base-labile N-8 acetyl group during DNA synthesis.