5'-O-(dimethoxytrityl)-2'-O-(tetrahydropyranyl)-N⁶-benzoyladenosine | 71933-61-4

• 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)-2'-O-(tetrahydropyranyl)-N⁶-benzoyladenosine
• 英文别名: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-3-(oxan-2-yloxy)oxolan-2-yl]purin-6-yl]benzamide
• CAS: 71933-61-4
• 化学式: C₄₃H₄₃N₅O₈
• 分子量: 757.843
• InChiKey: AWZXGCVVFNRKBI-BHBMXZPSSA-N

物化性质

• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5'-O-(dimethoxytrityl)-2'-O-(tetrahydropyranyl)-N⁶-benzoyladenosine 在 ammonium hydroxide 、 二异丙基铵盐四氮唑 作用下， 以 乙腈 为溶剂， 反应 31.0h， 生成 [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-(oxan-2-yloxy)oxolan-3-yl] [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate;azane
  参考文献：
  名称：

  Kierzek, Ryszard; Rozek, Marek; Markiewicz, Wojciech T., Bulletin of the Polish Academy of Sciences: Chemistry, 1987, vol. 35, # 11-12, p. 507 - 516

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-O-(1,1,3,3-四异丙基-1,3-二硅氧烷)腺苷 在 tri-n-butylamine hydrofluoride 、 对甲苯磺酸 作用下， 以 吡啶 为溶剂， 反应 38.33h， 生成 5'-O-(dimethoxytrityl)-2'-O-(tetrahydropyranyl)-N⁶-benzoyladenosine
  参考文献：
  名称：

  Oligonucleotide synthesis. Part 19. A convenient synthesis of the 3'-terminal nonaoligoribonucleotide of Rous Sarcoma virus 35S RNA via the modified phosphotriester approach

  摘要：

  DOI：

  10.1021/jo00157a001

文献信息

• 4-CHLOROPHENYL 5-CHLORO-8-QUINOLYL PHOSPHOROCHLORIDATE: A PRACTICALLY USEFUL PHOSPHORYLATING AGENT FOR OLIGORIBONUCLEOTIDE SYNTHESIS VIA PHOSPHOTRIESTER APPROACH
  作者：Hiroshi Takaku、Masatoshi Yoshida、Kazuo Kamaike、Tsuiiaki Hata

  DOI：10.1246/cl.1981.197

  日期：1981.2.5

  5′-O-Dimethoxytrityl-2′-O-tetrahydropyranylnucleosides (2) smoothly reacts with 4-chlorophenyl 5-chloro-8-quinolyl phosphorochloridate (1) prepared from 4-chlorophenyl phosphodichloridate and 5-chloro-8-hydroxyquinoline to give 5′-O-dimethoxytrityl-2′-O-tetrahydropyranylnucleoside 3′-(4-chlorophenyl, 5-chloro-8–quinolyl) phosphates (3) in high yields. They are key intermediates for the synthesis of

  5'-O-二甲氧基三苯甲基-2'-O-四氢吡喃基核苷 (2) 与 4-氯苯基 5-氯-8-喹啉基磷酸酯 (1) 顺利反应，由 4-氯苯基二氯代磷酸酯和 5-氯-8-羟基喹啉制备得到 5 '-O-二甲氧基三苯甲基-2'-O-四氢吡喃核苷 3'-（4-氯苯基，5-氯-8-喹啉基）磷酸酯 (3)，收率高。它们是通过磷酸三酯方法合成寡核糖核苷酸的关键中间体。
• 4-CHLOROPHENYL 5-CHLORO-8-QUINOLYL PHOSPHOROTETRAZOLIDE: A HIGHLY EFFICIENT PHOSPHORYLATING AGENT FOR OLIGORIBONUCLEOTIDE SYNTHESIS
  作者：Hiroshi Takaku、Tadaaki Nomoto、Kazuo Kamaike

  DOI：10.1246/cl.1981.543

  日期：1981.4.5

  phosphorotetrazolide (2) was a highly efficient phosphorylating agent for the synthesis of 5′-O-dimethoxytrityl-2′-O-tetrahydropyranylnucleoside 3′-(4-chlorophenyl, 5-chloro-8-quinolyl) phosphates (4). The fully protected ribonucleoside 3′-phosphotriesters 4 are key intermediates for the synthesis of oligoribonucleotides via phosphotriester approach.

  4-Chlorophenyl 5-chloro-8-quinolylphosphorotetrazolide (2) 是一种高效的磷酸化剂，用于合成 5'-O-dimethoxytrityl-2'-O-tetrahydropyranylnucleoside 3'-(4-chlorophenyl, 5-chloro-8 -喹啉)磷酸酯 (4)。完全保护的核糖核苷 3'-磷酸三酯 4 是通过磷酸三酯方法合成寡核糖核苷酸的关键中间体。
• 4-CHLOROPHENYL 5-CHLORO-8-QUINOLYL HYDROGEN PHOSPHATE: A USEFUL PHOSPHORYLATING AGENT FOR GUANOSINE 3′-PHOSPHOTRIESTER
  作者：Hiroshi Takaku、Kazuo Kamaike、Kenichi Kasuga

  DOI：10.1246/cl.1982.197

  日期：1982.2.5

  O-tetrahydropyranyl-N2-benzoylguanosine smoothly reacts with 4-chlorophenyl 5-chloro-8-quinolyl hydrogen phosphate in the presence of 8-quinolinesulfonyltetrazolide (QS-te) to give 5′-O-dimethoxytrityl-2′-O-tetrahydropyranyl-N2-benzoylguanosine 3′-(4-chlorophenyl, 5-chloro-8-quinolyl) phosphate in high yield without a side product such as O6-phosphorylated guanosine.

  5'-O-二甲氧基三苯甲基-2'-O-四氢吡喃基-N2-苯甲酰基鸟苷在8-喹啉磺酰四唑（QS-te）存在下与4-氯苯基5-氯-8-喹啉磷酸氢盐顺利反应生成5'-O -二甲氧基三苯甲基-2'-O-四氢吡喃基-N2-苯甲酰基鸟苷3'-（4-氯苯基，5-氯-8-喹啉基）磷酸酯，收率高，没有副产物如O6-磷酸化鸟苷。
• (Butylthio)carbonyl Group: A New Protecting Group for the Guanine Residue in Oligoribonucleotide Synthesis
  作者：Masayo Fujii、Shunichi Yamakage、Hiroshi Takaku、Tsujiaki Hata

  DOI：10.1016/s0040-4039(00)96821-7

  日期：1987.1

  The protection of the O6-amide and N2-amino groups of guanosine with the (butylthio)carbonyl group is described. This group could be rapidly introduced in good yields and removed very easily under the conventional deprotective condition for theexo-amino acyl groups of other nucleoside bases.

  描述了鸟苷的O 6-酰胺和N 2-氨基被（丁硫基）羰基保护。该基团可以以高收率快速引入，并且在常规脱保护条件下，对于其他核苷碱基的exo-氨基酰基，可以很容易地除去。
• Synthesis of Nonadeca- and Octadecaribonucleotides Using the Solid-Phase Phosphotriester with Tetrahydropyranyl Groups as the 2′-Hydroxyl-Protecting Group
  作者：Ichiro Hirao、Masahide Ishikawa、Hiroyuki Hori、Kimitsuna Watanabe、Kin-ichiro Miura

  DOI：10.1246/bcsj.62.1995

  日期：1989.6

  Nonadeca- and octadecaribonucleotides corresponding to the D-loop of tRNAPhe from yeast and the leader sequence of phage f1 coat protein mRNA were synthesized by the activated phosphotriester method. Coupling yield in the synthesis of oligoribonucleotides depended on the extent of nucleosides loaded on controlled pore glass beads (CPG). N-Acyl-5′-O-dimethoxytrityl-2′-O-tetrahydropyranyl derivatives were used as fully protected ribonucleotide monomer units. The 18mer and 19mer corresponding to the D-loop did not serve as substrates for tRNA (guanosine-2′-)methyltransferase from T. thermophilus, but inhibited methylation of the 5′-half fragment of tRNAPhe. This indicates that both fragments possess some affinity with the enzyme.

  通过活化的磷酸三酯法合成了对应于酵母tRNAPhe D环和噬菌体f1外壳蛋白mRNA引导序列的19-mer和18-mer非十聚体和十八聚体核酸。寡核糖核酸合成中的耦合产率依赖于加载在受控孔玻璃珠（CPG）上的核苷量。采用N-酰基-5′-O-二甲氧基三苯甲基-2′-O-四氢呋喃衍生物作为完全保护的核糖核苷单体单元。对应于D环的18mer和19mer并未作为T. thermophilus中tRNA（鸟苷-2′-）甲基转移酶的底物，但抑制了tRNAPhe的5′-半片段的甲基化。这表明这两个片段与该酶之间存在一定的亲和性。