(1S,2R,3S,4R)-N⁶-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydro-5-methylchrysenyl)>-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine | 1054312-69-4

• 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: (1S,2R,3S,4R)-N⁶-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydro-5-methylchrysenyl)>-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine
• 英文别名: [(1S,2R,3S,4R)-1,2-diacetyloxy-4-[[9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]purin-6-yl]amino]-5-methyl-1,2,3,4-tetrahydrochrysen-3-yl] acetate
• CAS: 1054312-69-4
• 化学式: C₄₇H₆₃N₅O₉Si₂
• 分子量: 898.216
• InChiKey: YGUGGIKCJBKSAJ-KTBUQPDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.78
• 重原子数：
  63
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4R)-N⁶-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydro-5-methylchrysenyl)>-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到(1S,2R,3S,4R)-N⁶-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydro-5-methylchrysenyl)>-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis of Oligonucleotide Adducts of the Bay Region Diol Epoxide Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons

  摘要：

  An efficient method for the site-specific synthesis of adducts between the biologically active diol epoxide metabolites of carcinogenic polycyclic aromatic hydrocarbons (PAHs) and oligonucleotides in which a PAH component of predetermined stereochemistry is linked covalently to the exocyclic amino groups of deoxyadenosine (dA) and deoxyguanosine (dG) is described. The synthetic strategy involves in the key step coupling a protected halopurine derivative with an amino derivative (or an aminotriol derivative) of the PAH. This method was initially employed to prepare the dA and dG adducts of the model PAH 1-methylpyrene. The appropriately protected dA adduct was then incorporated into the oligonucleotide sequence d(GCAGGTCA(*)AGAG) where A(*) represents N6-pyrenylmethyl-dA. This methodology was extended to the synthesis of trans adducts of anti-diol epoxide metabolites of benzo[a]pyrene and 5-methylchrysene linked to the 6-amino function of dA. The parent hydrocarbons are widespread environmental carcinogens. This synthetic approach, dubbed the total synthesis method, complements the direct synthesis method which involves the direct reaction of PAH diol epoxides with oligonucleotides. The total synthesis method is broader in scope than the latter, and it is readily adaptable to the large scale preparation of PAH-oligonucleotide adducts required for structure determination by high resolution NMR and X-ray crystallographic techniques.

  DOI：

  10.1021/jo00122a048
• 作为产物：
  描述：

  (+/-)-trans-1,2-Dihydroxy-anti-3,4-epoxy-1,2,3,4-tetrahydro-5-methylchrysene 在 palladium on activated charcoal 吡啶 、 sodium azide 、 六甲基二硅氧烷 、 异丁酰胺 、 氨 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0~65.0 ℃ 、48.26 kPa 条件下， 反应 126.17h， 生成 (1S,2R,3S,4R)-N⁶-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydro-5-methylchrysenyl)>-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis of Oligonucleotide Adducts of the Bay Region Diol Epoxide Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons

  摘要：

  An efficient method for the site-specific synthesis of adducts between the biologically active diol epoxide metabolites of carcinogenic polycyclic aromatic hydrocarbons (PAHs) and oligonucleotides in which a PAH component of predetermined stereochemistry is linked covalently to the exocyclic amino groups of deoxyadenosine (dA) and deoxyguanosine (dG) is described. The synthetic strategy involves in the key step coupling a protected halopurine derivative with an amino derivative (or an aminotriol derivative) of the PAH. This method was initially employed to prepare the dA and dG adducts of the model PAH 1-methylpyrene. The appropriately protected dA adduct was then incorporated into the oligonucleotide sequence d(GCAGGTCA(*)AGAG) where A(*) represents N6-pyrenylmethyl-dA. This methodology was extended to the synthesis of trans adducts of anti-diol epoxide metabolites of benzo[a]pyrene and 5-methylchrysene linked to the 6-amino function of dA. The parent hydrocarbons are widespread environmental carcinogens. This synthetic approach, dubbed the total synthesis method, complements the direct synthesis method which involves the direct reaction of PAH diol epoxides with oligonucleotides. The total synthesis method is broader in scope than the latter, and it is readily adaptable to the large scale preparation of PAH-oligonucleotide adducts required for structure determination by high resolution NMR and X-ray crystallographic techniques.

  DOI：

  10.1021/jo00122a048