Phosphoric acid (2R,3S,5R)-2-hydroxymethyl-5-[6-((7R,8S,9R,10R)-7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-ylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester bis-[2-(4-nitro-phenyl)-ethyl] ester | 174060-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: Phosphoric acid (2R,3S,5R)-2-hydroxymethyl-5-[6-((7R,8S,9R,10R)-7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-ylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester bis-[2-(4-nitro-phenyl)-ethyl] ester
• 英文别名: [(2R,3S,5R)-2-(hydroxymethyl)-5-[6-[[(7R,8S,9R,10R)-7,8,9-trihydroxy-7,8,9,10-tetrahydrobenzo[a]pyren-10-yl]amino]purin-9-yl]oxolan-3-yl] bis[2-(4-nitrophenyl)ethyl] phosphate
• CAS: 174060-76-5
• 化学式: C₄₆H₄₂N₇O₁₃P
• 分子量: 931.852
• InChiKey: GQYVMHRZCIZXRF-SQCZHOIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  67
• 可旋转键数：
  14
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  282
• 氢给体数：
  5
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  Phosphoric acid (2R,3S,5R)-2-hydroxymethyl-5-[6-((7R,8S,9R,10R)-7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-ylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester bis-[2-(4-nitro-phenyl)-ethyl] ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 为溶剂， 反应 24.0h， 生成 Phosphoric acid mono-{(2R,3S,5R)-2-hydroxymethyl-5-[6-((7R,8S,9R,10R)-7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-ylamino)-purin-9-yl]-tetrahydro-furan-3-yl} ester
  参考文献：
  名称：

  Synthesis of Deoxyadenosine 3‘-Phosphates Bearing Cis and Trans Adducts of 7β,8α-Dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene:  Standards for ³²P-Postlabeling Assays

  摘要：

  Deoxyadenosine 3'-phosphates bearing cis and trans N-6 adducts of (7R) and (7S)-anti 7 beta,8 alpha-dihydroxy-9 alpha,10 alpha-epoxy-7,8,9, 10-tetrahydrobenzo[alpha]pyrenes have been prepared in good yield by reaction of 6-fluoropurinyl 2'-deoxyriboside 3'-(bis(2-[4-nitrophenyl]ethyl)phosphate with the (+/-)(7 beta,8 alpha,9 alpha,10 beta)- and (+/-)-(7 beta,8 alpha,9 alpha,10 alpha)-10-amino-7,8,9,10-tetrahydrobenzo[alpha]pyrene-7,8,9-triols. The protected phosphates are easily prepared as diasteromeric mixtures, readily resolved by reversed phase HPLC, and efficiently deprotected with DBU to give the adducted S'-phosphates. These nucleotides are of value as standards for the P-32-postlabeling procedure of Randerath for determination of benzo[alpha]pyrene adducts in DNA (Reddy et al. Carcinogenesis 1984, 5, 231).

  DOI：

  10.1021/jo9510898
• 作为产物：
  描述：

  Phosphoric acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-chloro-purin-9-yl)-tetrahydro-furan-3-yl ester bis-[2-(4-nitro-phenyl)-ethyl] ester 在 potassium fluoride 、 三异丁基铝 、 溶剂黄146 、 三甲胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 124.17h， 生成 Phosphoric acid (2R,3S,5R)-2-hydroxymethyl-5-[6-((7R,8S,9R,10R)-7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-ylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester bis-[2-(4-nitro-phenyl)-ethyl] ester
  参考文献：
  名称：

  Synthesis of Deoxyadenosine 3‘-Phosphates Bearing Cis and Trans Adducts of 7β,8α-Dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene:  Standards for ³²P-Postlabeling Assays

  摘要：

  Deoxyadenosine 3'-phosphates bearing cis and trans N-6 adducts of (7R) and (7S)-anti 7 beta,8 alpha-dihydroxy-9 alpha,10 alpha-epoxy-7,8,9, 10-tetrahydrobenzo[alpha]pyrenes have been prepared in good yield by reaction of 6-fluoropurinyl 2'-deoxyriboside 3'-(bis(2-[4-nitrophenyl]ethyl)phosphate with the (+/-)(7 beta,8 alpha,9 alpha,10 beta)- and (+/-)-(7 beta,8 alpha,9 alpha,10 alpha)-10-amino-7,8,9,10-tetrahydrobenzo[alpha]pyrene-7,8,9-triols. The protected phosphates are easily prepared as diasteromeric mixtures, readily resolved by reversed phase HPLC, and efficiently deprotected with DBU to give the adducted S'-phosphates. These nucleotides are of value as standards for the P-32-postlabeling procedure of Randerath for determination of benzo[alpha]pyrene adducts in DNA (Reddy et al. Carcinogenesis 1984, 5, 231).

  DOI：

  10.1021/jo9510898

文献信息

• Synthesis of Deoxyadenosine 3‘-Phosphates Bearing <i>Cis</i> and <i>Trans</i> Adducts of 7β,8α-Dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[<i>a</i>]pyrene:  Standards for ³²P-Postlabeling Assays
  作者：Shin Han、Constance M. Harris、Thomas M. Harris、Hye-Young Hong Kim、Seong J. Kim

  DOI：10.1021/jo9510898

  日期：1996.1.1

  Deoxyadenosine 3'-phosphates bearing cis and trans N-6 adducts of (7R) and (7S)-anti 7 beta,8 alpha-dihydroxy-9 alpha,10 alpha-epoxy-7,8,9, 10-tetrahydrobenzo[alpha]pyrenes have been prepared in good yield by reaction of 6-fluoropurinyl 2'-deoxyriboside 3'-(bis(2-[4-nitrophenyl]ethyl)phosphate with the (+/-)(7 beta,8 alpha,9 alpha,10 beta)- and (+/-)-(7 beta,8 alpha,9 alpha,10 alpha)-10-amino-7,8,9,10-tetrahydrobenzo[alpha]pyrene-7,8,9-triols. The protected phosphates are easily prepared as diasteromeric mixtures, readily resolved by reversed phase HPLC, and efficiently deprotected with DBU to give the adducted S'-phosphates. These nucleotides are of value as standards for the P-32-postlabeling procedure of Randerath for determination of benzo[alpha]pyrene adducts in DNA (Reddy et al. Carcinogenesis 1984, 5, 231).