8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine | 479408-35-0

• 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: 8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine
• 英文别名: N-[2-amino-9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-6-phenylmethoxypurin-8-yl]-N-(9H-fluoren-2-yl)acetamide
• CAS: 479408-35-0
• 化学式: C₄₄H₅₈N₆O₅Si₂
• 分子量: 807.153
• InChiKey: BVYCGAGWWJAVIG-HKIDPNTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.94
• 重原子数：
  57
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine 在 palladium on activated charcoal 四丁基氟化铵 、 溶剂黄146 、 环己烯 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 为溶剂， 反应 3.0h， 生成 8-(N-acetyl-2-amino-fluorene)-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 tris-(dibenzylideneacetone)dipalladium(0) 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 、 三苯基膦 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 甲苯 为溶剂， 反应 11.0h， 生成 8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-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

• 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.