3'-acetyl-5'-O-DMT-N²-isobutyryl-2'-deoxyguanosine | 93130-36-0

• 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: 3'-acetyl-5'-O-DMT-N²-isobutyryl-2'-deoxyguanosine
• 英文别名: [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] acetate
• CAS: 93130-36-0
• 化学式: C₃₇H₃₉N₅O₈
• 分子量: 681.745
• InChiKey: QULRBMKSQKJCOR-OJDZSJEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  50
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3'-acetyl-5'-O-DMT-N²-isobutyryl-2'-deoxyguanosine 在 ammonium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 生成 5'-DMTr-N2-isobutyryl-O6(2-pyridyl)methyl-2'-deoxyguanosine
  参考文献：
  名称：

  Awasthi, S. K.; Khanna, V.; Watal, G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 9, p. 916 - 919

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 在 4-二甲氨基吡啶 、 TEA 作用下， 以 吡啶 为溶剂， 反应 3.0h， 生成 3'-acetyl-5'-O-DMT-N²-isobutyryl-2'-deoxyguanosine
  参考文献：
  名称：

  Awasthi, S. K.; Khanna, V.; Watal, G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 9, p. 916 - 919

  摘要：

  DOI：

文献信息

• Improved Synthesis of Oligodeoxyribonucleotides by Solid-Phase Phosphotriester Method UtilizingO6-[2-(p-Nitrophenyl)ethyl]-2?-deoxyguanosine Derivatives
  作者：Andr� Chollet、Edgar Ayala、Eric H. Kawashima

  DOI：10.1002/hlca.19840670521

  日期：1984.8.8

  The synthesis of oligodeoxyribonucleotides on a cross-linked polystyrene solid support utilizing stable mono- and dinucleotide phosphotriester building blocks is presented. The use of O6[2-(p-nitrophenyl)ethyl]-2′-deoxyguanosine derivatives yields cleaner DNA fragments by suppressing side reactions. Modifications improving the phosphotriester methodology are presented. The purification methods and

  提出了利用稳定的单核苷酸和二核苷酸磷酸三酯结构单元在交联的聚苯乙烯固体载体上合成寡脱氧核糖核苷酸。使用ö 6 [2-（p通过抑制副反应硝基苯基）乙基] -2'-脱氧鸟苷的产率衍生物吸尘器的DNA片段。提出了改进磷酸三酯方法的修饰。描述了合成寡聚脱氧核糖核苷酸的纯化方法和分析。
• Kumar, Prabhat; Singh; Misra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 7, p. 657 - 661
  作者：Kumar, Prabhat、Singh、Misra

  DOI：——

  日期：——
• 2-(4-Nitrophenyl)ethyl Methylenebis(phosphonate):  A Versatile Reagent for the Synthesis of Nucleoside 5‘-Methylenebis(phosphonate)s
  作者：Krystyna Lesiak、Kyoichi A. Watanabe、Jay George、Krzysztof W. Pankiewicz

  DOI：10.1021/jo971859a

  日期：1998.3.1

  2-(4-Nitrophenyl)ethyl methylenebis(phosphonate) (6) was prepared by reaction of equimolar amounts of 2-(4-nitrophenyl)ethyl alcohol and methylenebis(phosphonyl) tetrachloride in the presence of tetrazole. Compound 6 was further converted into the corresponding 4-nitrophenylethyl trisanhydride intermediate 7 by dehydration with diisopropylcarbodiimide (DIC). Reaction of 7 with either 2',3'-O-isopropylideneadenosine (8a) or 2',3'-O-isopropylideneguanosine (8b) afforded, after hydrolysis, the desired P-1-[2-(4-nitrophenyl)ethyl]-P-2-(2',3'-O-isopropylideneadenosin-5'-yl)methylenebis(phosphonate) (9a) and guanosine analogue 9b, respectively. A similar treatment of intermediate 7 with 3'-O-acetylthymidine (12a), 3'-O-acetyl-2'-deoxy-N-4-benzoylcytidine (12b), 3'-O-acetyl-2'-deoxy-N-6-benzoyladenosine (12c), and 3'-O-acetyl-2'-deoxy-N-2-isobutyrylguanosine (12d) gave the corresponding 2-(4-nitrophenyl)ethyl methylenebis(phosphonate)s 13a-d. These compounds as well as 9a,b were treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) which caused elimination of the 2-(4-nitrophenyl)ethyl group. The base labile 3'-O-acetyl, N-4-acetyl, N-6-benzoyl, and N-2-isobutyryl groups of 12a-d were also removed during the DBU treatment. Thus, the 5'-methylenebis(phosphonate)s of 2',3'-O-isopropylideneadenosine (10a), 2',3'-O-isopropylideneguanosine (10b), thymidine (14a), 2'-deoxycytidine (14b), 2'-deoxyadenosine (14c), and 2'-deoxyguanosine (14d) were prepared in good yield. De-O-isopropylidenation of 10a and 10b afforded adenosine 5'-methylenebis(phosphonate) (11a) and guanosine 5'-methylenebis(phosphonate) (11b), respectively.
• Necessary protection of the O6-position of guanine during the solid phase synthesis of oligonucleotides by the phosphoramidite approach
  作者：Richard T. Pon、Masad J. Damha、Kelvin K. Ogilvie

  DOI：10.1016/s0040-4039(00)98827-0

  日期：1985.1