5'-O-(Methoxytrityl)-N²-isobutyryldeoxyguanosine | 59321-92-5

• 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-(Methoxytrityl)-N²-isobutyryldeoxyguanosine
• 英文别名: 5'-O-monomethoxytrityl-N-isobutyryldeoxyquanosine；N²-isobutyryl-5'-O-monomethoxytrityl-2'-desoxyguanosin；N²-Isobutyryl-5'-O-monomethoxytrityl-2'-deoxyguanosine；dMeOTribG；N-[9-[(2R,4S,5R)-4-hydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 59321-92-5
• 化学式: C₃₄H₃₅N₅O₆
• 分子量: 609.682
• InChiKey: FQTPONUNZDHSNX-UPRLRBBYSA-N

物化性质

• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-(Methoxytrityl)-N²-isobutyryldeoxyguanosine 在 ammonium hydroxide 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.33h， 生成 Phosphoric acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester; compound with triethyl-amine
  参考文献：
  名称：

  环状烯二醇磷酸化法合成脱氧核糖四核苷酸

  摘要：

  给出了磷酸二酯合成的二（1,2-二甲基亚乙基亚乙基）焦磷酸盐方法在dG，dA，dC和dT家族中将脱氧核糖核苷转化为脱氧核糖二核苷酸的完整实验细节。作为用于将脱氧核糖二核苷酸转化为脱氧核糖四核苷酸的试剂，N-（1,2-二甲基亚乙二基二氧基磷酰基）咪唑优于相应的焦磷酸盐。

  DOI：

  10.1016/s0040-4020(01)91932-5
• 作为产物：
  描述：

  N²,3',5'-triisobutyryl-2'-deoxyguanosine 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.25h， 生成 5'-O-(Methoxytrityl)-N²-isobutyryldeoxyguanosine
  参考文献：
  名称：

  Nucleotides; XXIII¹Synthesis of Protected 2′-Deoxyribonucleoside-3′,-phosphotriesters containing thep-Nitrophenylethyl Phosphate Blocking Group

  摘要：

  DOI：

  10.1055/s-1984-31040

文献信息

• Tritylation of alcohols under mild conditions without using silver salts
  作者：Shahien Shahsavari、Jinsen Chen、Travis Wigstrom、James Gooding、Alexander Gauronskas、Shiyue Fang

  DOI：10.1016/j.tetlet.2016.07.062

  日期：2016.8

  Secondary alcohols were conveniently tritylated under mild conditions within a short running time with tritylium trifluoroacetate generated in situ from trityl alcohols and trifluoroacetic anhydride. No expensive silver salts were needed for the reactions. Four secondary alcohols were tritylated with both mono- and dimethoxy trityl alcohols giving good to excellent isolated yields. The reaction was

  在温和条件下，在短运行时间内，将三醇方便地与由三苯甲醇和三氟乙酸酐原位生成的三氟乙酸三苯乙铵进行三苯甲基化。反应不需要昂贵的银盐。四种仲醇与单和二甲氧基三苯甲基醇一起三苯甲基化，具有良好的优异分离产率。还对具有伯醇的四种核苷衍生物测试了该反应。还获得令人满意的结果。
• Studies on deoxynucleic acids and related compounds. VI. Synthesis of oligodeoxyribonucleotides containing recognition sequences for restriction endonucleases.
  作者：EIKO OHTSUKA、SUSUMU SHIBAHARA、MORIO IKEHARA

  DOI：10.1248/cpb.30.1307

  日期：——

  An octanucleotide dACCCGGGT and decanucleotide dCGACCCGGGT have been synthesized by an improved phosphotriester method. The octanucleotide has a selfcomplementary sequence and the decanucleotide has two protruding nucleotides when it forms a duplex. Thermal properties and circular dichroism spectra of these oligonucleotides have been investigated under various conditions to find differences in the stabilities of these oligonucleotides. A possible concatemer structure of the decanucleotide duplex is suggested on the basis of its circular dichroism spectra in concentrated solution.

  通过改进的磷三酯方法合成了八聚核苷酸 dACCCGGGT 和十聚核苷酸 dCGACCCGGGT。八聚核苷酸具有自我互补的序列，而十聚核苷酸在形成双链时有两个突出核苷酸。对这些寡核苷酸的热学性质和圆二色谱进行了研究，以寻找这些寡核苷酸稳定性之间的差异。基于其在浓缩溶液中的圆二色谱，提出了十聚核苷酸双链的一个可能的聚合体结构。
• A simplified strategy for the synthesis of dideoxyribonucleotide blocks
  作者：K.L. Sadana、F.E. Hruska、P.C. Loewen

  DOI：10.1016/s0040-4039(01)81907-9

  日期：1981.1

  The rapid synthesis of dideoxyribonucleotide blocks in 60–85% isolated yields has been achieved by combining the phosphorylation and condensation steps in a sequential reaction series which also allows the recovery of unreacted nucleotides.

  通过将磷酸化和缩合步骤结合在顺序反应系列中，已实现了60-85％分离产率的双脱氧核糖核苷酸嵌段的快速合成，这也允许回收未反应的核苷酸。
• A CONVENIENT PROCEDURE FOR THE PREPARATION OF DINUCLEOSIDE PHOSPHATES By THE USE OF A BIFUNCTIONAL PHOSPHORYLATING REAGENTS, 2-CHLOROPHENYLPHOSPHOROBIS(NITROBENZOTRIAZOLIDE)
  作者：Oyo Mitsunobu、Miyako Takahashi、Hiroshi Seki、Makoto Arai、Fumiko Yasumoto、Hideaki Iwami、Naoto Kawakami、Junko Kamishiro

  DOI：10.1246/cl.1985.949

  日期：1985.7.5

  The reagent formed By the reaction of 2-chlorophenyl phosphorodichloridate with 2 molar amounts of 5-nitrobenzotriazole was allowed to react successively with nucleosides having free 3′-hydroxyl groups and nucleosides having free 5′-hydroxyl groups affording the corresponding dinucleoside phosphates in 63–97% yields.

  2-chlorophenyl phosphorodichloridate 与 2 摩尔量的 5-nitrobenzotriazole 反应生成的试剂先后与具有游离 3′-hydroxyl 基团的核苷和具有游离 5′-hydroxyl 基团的核苷反应，得到相应的二核苷磷酸酯，产率为 63-97%。
• Nucleoside und Nucleotide. Teil 14. Synthese des Octanucleosidheptaphosphats d(G-A-T-T-T-T-G-A)
  作者：Peter Bühlmayer、Georg Graf、Felix Waldmeier、Christoph Tamm

  DOI：10.1002/hlca.19800630841

  日期：1980.12.10

  Nucleosides and Nucleotides. Part 14. Synthesis of the Octanucleosideheptaphosphate d(G-A-T-T-T-T-G-A)

  核苷和核苷酸。第14部分。八核苷七磷酸d（GATTTTGA）的合成