4-Oxo-pentanoic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester | 86710-51-2

• 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: 4-Oxo-pentanoic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[2-(2-methylpropanoylamino)-6-oxo-3H-purin-9-yl]oxolan-3-yl] 4-oxopentanoate
• CAS: 86710-51-2
• 化学式: C₄₀H₄₃N₅O₉
• 分子量: 737.81
• InChiKey: GNQNDCSJZWWUPY-WIHCDAFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  54.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  172.96
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4-Oxo-pentanoic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 在 四氮唑 、 碘 、 溶剂黄146 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  Improvements in oligodeoxyribonucleotide synthesis: methyl N,N-dialkylphosphoramidite dimer units for solid support phosphite methodology

  摘要：

  DOI：

  10.1021/jo00199a032
• 作为产物：
  描述：

  当归内酯 、 N2-异丁酰-5'-O-(4,4'-二甲氧基三苯基)-2'-脱氧鸟苷 反应 5.0h， 生成 4-Oxo-pentanoic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Oligodeoxyribonucleotide Phosphorothioates: Substantial Reduction of (N-1)-mer Content Through the Use of Trimeric Phosphoramidite Synthons

  摘要：

  Use of fully protected trimeric phosphoramidite synthons in the synthesis of oligonucleotide phosphorothioate shows a substantial reduction (>85%) in (n-1)-mer content as compared to oligomers synthesized through coupling of standard phosphoramidite monomers. A 20-mer oligodeoxyribonucleotide phosphorothioate which is in phase I clinical trials was chosen as an example for the studies.

  DOI：

  10.1080/15257779908043091

文献信息

• The influence of the purine 2-amino group on DNA conformation and stability-II
  作者：Barbara L. Gaffney、Luis A. Marky、Roger A. Jones

  DOI：10.1016/0040-4020(84)85098-x

  日期：1984.1

  Synthesis of an N-protected derivative of 2-amino-2'-deoxyadenosine (dA') from 2'-deoxyguanosine is reported. The syntheses of several oligodeoxynucleotides containing this modified nucleoside are described, together with physical characterization via melting studies and CD conformational analysis. As expected, the 2-amino group is seen to add to the duplex stability. Although the sequence d(TA')3

  据报道，由2'-脱氧鸟苷合成了N-保护的2-氨基-2'-脱氧腺苷（dA'）衍生物。描述了几种含有这种修饰核苷的寡聚脱氧核苷酸的合成，以及通过熔解研究和CD构象分析的物理表征。如所预期的，看到2-氨基基团增加了双链体的稳定性。尽管发现序列d（TA'）3经历了盐诱导的构象转变，但是诸如d（CGTA'CG）的混合序列却没有表现出这种行为。这些序列中存在的所有鸟嘌呤残基均为O 6用氰基乙基或4-硝基苯基乙基进行保护，以消除鸟嘌呤在磷酸化和缩合反应中的降解。描述了引入和除去这些O 6保护基的方法。
• 2,2,5,5-Tetramethylpyrrolidin-3-one-1-sulfinyl Group for 5‘-Hydroxyl Protection of Deoxyribonucleoside Phosphoramidites in the Solid-Phase Preparation of DNA Oligonucleotides
  作者：Vicente Marchán、Jacek Cieślak、Victor Livengood、Serge L. Beaucage

  DOI：10.1021/ja048377i

  日期：2004.8.1

  nitrogen-sulfur reagents have been investigated as potential 5'-hydroxyl protecting groups for deoxyribonucleoside phosphoramidites to improve the synthesis of oligonucleotides on glass microarrays. Out of the nitrogen-sulfur-based protecting groups so far investigated, the 2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl group exhibited near optimal properties for 5'-hydroxyl protection by virtue of the

  已经研究了几种氮硫试剂作为脱氧核糖核苷亚磷酰胺的潜在 5'-羟基保护基团，以改善玻璃微阵列上寡核苷酸的合成。在迄今为止研究的氮硫基保护基团中，2,2,5,5-四甲基吡咯烷-3-one-1-亚磺酰基由于其温和性而表现出近乎最佳的 5'-羟基保护性质。脱保护条件。具体而言，在控制孔玻璃上合成 5'-d(ATCCGTAGCCAAGGTCATGT) 时，末端 5'-亚磺酰胺基团的迭代裂解是通过在酸性盐的存在下用碘处理来有效完成的。寡核苷酸水解为其 2' -脱氧核糖核苷暴露于蛇毒磷酸二酯酶和细菌碱性磷酸酶后未显示任何核碱基加合物或其他修饰的形成。这些发现表明，用于亚磷酰胺 5'-羟基保护的 2,2,5,5-四甲基吡咯烷-3-one-1-亚磺酰基，如 10a-d，可能导致寡核苷酸微阵列的产生，其表现出增强的特异性和检测核酸靶标的灵敏度。
• On the formation of longmers in phosphorothioate oligodeoxyribonucleotide synthesis
  作者：Achim H. Krotz、Patrick G. Klopchin、Kathleen L. Walker、G.Susan Srivatsa、Douglas L. Cole、Vasulinga T. Ravikumar

  DOI：10.1016/s0040-4039(97)00798-3

  日期：1997.6

  The extent of longmer formation in phosphorothioate oligodeoxyribonucleotide synthesis through amidite chemistry on solid support depends on base composition, contact time and acidity of the promotor used for activation of the phosphoramidite, A longmer formation mechanism that involves dedimethoxytritylation of the phosphite triester intermediate is proposed. (C) 1997 Elsevier Science Ltd.