5'-O-dimethoxytrityl-N²-isobutyryl-O⁶-<2-(p-nitrophenyl)ethyl>-2'-deoxyguanosine | 90678-72-1

• 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: 5'-O-dimethoxytrityl-N²-isobutyryl-O⁶-<2-(p-nitrophenyl)ethyl>-2'-deoxyguanosine
• 英文别名: 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N²-isobutyryl-O⁶-[2-(4-nitrophenyl)ethyl]guanosine；5'-O-(dimethoxytrityl)-2-N-isobutyryl-6-O-<2-(4-nitrophenyl)ethyl>2'-deoxyguanosine；2-N-isobutyryl-6-O-(4-nitrophenylethyl)-5'-O-dimethoxytrityl-2'-deoxyguanosine；N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-6-[2-(4-nitrophenyl)ethoxy]purin-2-yl]-2-methylpropanamide
• CAS: 90678-72-1
• 化学式: C₄₃H₄₄N₆O₉
• 分子量: 788.857
• InChiKey: JOILMBMYRCKAAB-HKIDPNTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  58
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5'-O-dimethoxytrityl-N²-isobutyryl-O⁶-<2-(p-nitrophenyl)ethyl>-2'-deoxyguanosine 生成 [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[2-(2-methylpropanoylamino)-6-[2-(4-nitrophenyl)ethoxy]purin-9-yl]oxolan-3-yl]oxyphosphinic acid
  参考文献：
  名称：

  TOCIK, Z.;ARNOLD, L.;SMRT, J., 7TH SYMP. CHEM. NUCL. ACID COMPON., BECHYNE CASTLE, AUG. 30TH - SEPT. 5TH+

  摘要：

  DOI：
• 作为产物：
  描述：

  4-Oxo-pentanoic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-{2-isobutyrylamino-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-3-yl ester 在 一水合肼 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 0.5h， 以91%的产率得到5'-O-dimethoxytrityl-N²-isobutyryl-O⁶-<2-(p-nitrophenyl)ethyl>-2'-deoxyguanosine
  参考文献：
  名称：

  嘌呤2-氨基对DNA构象和稳定性的影响-II：d [CGT（2-NH 2）ACG]，d [CGU（2-NH 2）ACG]和d [CGT的合成和物理表征（2-NH 2）AT（2-NH 2）ACG]

  摘要：

  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。

  DOI：

  10.1016/0040-4020(84)85098-x

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。
• Transient protection. 2. One-flask synthesis of 6-O-[(4-nitrophenyl)ethyl]-2'-deoxyguanosine nucleosides
  作者：Xiaolian Gao、Barbara L. Gaffney、Susan Hadden、Roger A. Jones

  DOI：10.1021/jo00355a038

  日期：1986.3
• Nucleotides, Part LXIII, New 2-(4-Nitrophenyl)ethyl(Npe)- and 2-(4-Nitrophenyl)ethoxycarbonyl(Npeoc)-Protected 2′-Deoxyribonucleosides and Their 3′-Phosphoramidites - Versatile Building Blocks for Oligonucleotide Synthesis
  作者：Holger Lang、Margarete Gottlieb、Michael Schwarz、Silke Farkas、Bernd S. Schulz、Frank Himmelsbach、Ramamurthy Charubala、Wolfgang Pfleiderer

  DOI：10.1002/(sici)1522-2675(19991215)82:12<2172::aid-hlca2172>3.0.co;2-r

  日期：1999.12.15

  A series of new base-protected and 5'-O-(4-monomethoxytrityl)- or 5'-O-(4,4'-dimethoxytrityl)-substituted 3'-(2-cyanoethyl diisopropylphosphoramidites) and 3'-[2-(4-nitrophenyl)ethyl diisopropylphosphoramidites] 52-66 and 67-82, respectively, are prepared as potential building blocks for oligonucleotide synthesis (see Scheme). Thus, 3',5'-di-O-acyl- and N-2,3'-O,5'-O-triacyl-2'-deoxyguanosines can easily be converted into the corresponding O-6-alkyl derivatives 6, 8, 10, 12, 14, and 16 by a Mitsunobu reaction using the appropriate alcohol. Mild hydrolysis removes the acyl groups from the sugar moiety (--> 9, 11, 13, 15, and 19 (via 18), resp.) which can then be tritylated (--> 38-42) and phosphitylated (--> 57-61) in the usual manner. N-2-[2-(4-nitrophenyl)ethoxycarbonyl]-substituted and N-2-[2-(4-nitrophenyl)ethoxycarbonyl]-O-6-[2-(4-nitrophenyl)ethyl]-substituted 2'-deoxyguanosines 5 and 7, respectively, are synthesized as new starting materials for tritylation (--> 28, 35, and 37) and phosphitylation (--> 54, 56, 70, and 78). Various O-4-alkylthymidines (see 20-24) are also converted to their 5'-O-dimethoxytrityl derivatives (see 43-47) and the corresponding phosphoramidites (see 62-66 and 79-82).
• Francois, P.; Hamoir, G.; Sonveaux, E., Bulletin des Societes Chimiques Belges, 1985, vol. 94, # 11-12, p. 821 - 824
  作者：Francois, P.、Hamoir, G.、Sonveaux, E.、Vermeersch, H.、Ma, Y.

  DOI：——

  日期：——
• Nielsen, J.; Marugg, J. E.; Taagaard, M., Recueil des Travaux Chimiques des Pays-Bas, 1986, vol. 105, # 1, p. 33 - 34
  作者：Nielsen, J.、Marugg, J. E.、Taagaard, M.、Boom, J. H. van、Dahl, O.

  DOI：——

  日期：——