N-[6-Benzyloxy-9-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-(9H-fluoren-2-ylamino)-9H-purin-2-yl]-2-(4-isopropyl-phenoxy)-acetamide | 479408-40-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: N-[6-Benzyloxy-9-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-(9H-fluoren-2-ylamino)-9H-purin-2-yl]-2-(4-isopropyl-phenoxy)-acetamide
• CAS: 479408-40-7
• 化学式: C₅₃H₆₈N₆O₆Si₂
• 分子量: 941.331
• InChiKey: JIDVQDSAQDGIMA-UFCNIINJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.56
• 重原子数：
  67.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  130.88
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-[6-Benzyloxy-9-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-(9H-fluoren-2-ylamino)-9H-purin-2-yl]-2-(4-isopropyl-phenoxy)-acetamide 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 、 二异丙胺 、 环己烯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 51.0h， 生成 N-[2-氨基-9-[(4S,5R)-4-羟基-5-(羟基甲基)四氢呋喃-2-基]-6-氧代-3H-嘌呤-8-基]-N-(9H-芴-2-基)乙酰胺
  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：

  2-氨基芴 、 N-{6-Benzyloxy-8-bromo-9-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-2-yl}-2-(4-isopropyl-phenoxy)-acetamide 在 tris(dibenzylideneacetone)dipalladium (0) 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 120.0h， 以70%的产率得到N-[6-Benzyloxy-9-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-(9H-fluoren-2-ylamino)-9H-purin-2-yl]-2-(4-isopropyl-phenoxy)-acetamide
  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