[(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl] (4-chlorophenyl) phosphate | 71100-59-9

• 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: [(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl] (4-chlorophenyl) phosphate
• CAS: 71100-59-9
• 化学式: C₄₄H₃₈ClN₅O₉P
• 分子量: 847.241
• InChiKey: LIAGVWFOSLFWSX-LCKTVPPXSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  60
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl] (4-chlorophenyl) phosphate 在 四氮唑 、 2,4,6-三异丙基苯磺酰氯 、 zinc dibromide 作用下， 以 吡啶 、 二氯甲烷 、 异丙醇 为溶剂， 反应 24.33h， 生成
  参考文献：
  名称：

  The Evaluation OF 2′, 3′-Dideoxy-β-D-Erythro-Hex-2′-Enopyranosyl Nucleosides as Potential Antisense Constructs: Synthesis, Biophysical Properties and Enzymatic Stability of 2′-Deoxyadenosine-(3′–6′)-[1-(2′, 3′-Dideoxy-β-D-Erythro-Hex-2′-Enopyranosyl)thymine] Phosphate

  摘要：

  1-(2',3'-dideoxy-beta-D-erythro-hex-2'-enopryanosyl)thymine was used as a nucleoside substitute in the synthesis of the dimer ApT*. CD studies on the dimer show that it adopts stacked, B-form mini-helices in solution. The title compound, relative to natural ApT, possesses an increased resistance to degradation by nucleases.

  DOI：

  10.1080/15257779508014661
• 作为产物：
  描述：

  5'-O-(dimethoxytrityl)-N-benzoyladenine 3'-(p-chlorophenylcyanoethyl phosphate) 在 二异丙胺 作用下， 以 吡啶 为溶剂， 反应 0.6h， 生成 [(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl] (4-chlorophenyl) phosphate
  参考文献：
  名称：

  Modified phosphotriester method for chemical synthesis of ribooligonucleotides. Part I. Synthesis of riboundecaadenylate and two fragments constituting the sequence of R-17 translation control signal

  摘要：

  一种改良的磷酸三酯方法已成功应用于核糖寡核苷酸的化学合成。起始物是含有3'-磷酸三酯基团的完全保护的核糖单核苷酸。偶联反应使用二甲苯磺酰四唑进行，并通过反相柱层析纯化产物。该方法的有效性已通过成功合成r-A₇、r-A₁₁、r5′-AAACAUGAGGA-3′和r5′-UUACCCAUGU-3′（R-17，翻译控制序列）来证明。

  DOI：

  10.1139/v82-021

文献信息

• Studies on deoxyribonucleic acids and related compounds. III. Synthesis of oligodeoxyribonucleotides complementary to the anticodon loop of Escherichia coli tRNA by an improved triester method.
  作者：EIKO OHTSUKA、SUSUMU SHIBAHARA、MORIO IKEHARA

  DOI：10.1248/cpb.29.3440

  日期：——

  p-Chlorophenyl N-(p-methoxyphenyl) chlorophosphoramidate was used to phosphorylate the 3'-hydroxyl groups of N, 5'-O-protected deoxyribonucleosides. These nucleotides served as the 3'-terminal unit in the synthesis of fully protected oligonucleotides, and the p-anisidine was readily removed by treatment with isoamyl nitrite to generate the 3'-phosphodiester for condensations. This approach was suitable for complete purification of fully protected oligonucleotides by chromatography, which was essential to obtain products. Deoxyoligonucleotides complementary to the anticodon loop of E. coli tRNAMetf were synthesized by condensation of di-, tri- and tetranucleotide blocks (dATp, dTATp and dTTATp) with protected dGAG. The products (dA-T-G-A-G, d-T-A-T-G-A-G and d-T-T-A-T-G-A-G) were isolated by anion-exchange or reverse phase high pressure liquid chromatography.

  p-氯苯基 N-(对甲氧苯基)氯代磷酰胺酯被用来磷酸化N,5'-O-保护的脱氧核苷的3'-羟基。这些核苷酸作为合成全保护的寡脱氧核苷酸的3'-末端单元，而对甲氧基苯胺可便利地通过用异戊基亚硝酸盐处理来除去，生成用于缩合的3'-磷酸二酯。这种方法适合通过色谱法对全保护的寡脱氧核苷酸进行完全纯化，这是获取产品的关键。通过将二、三和四核苷酸块(dATP、dTATP和dTTATP)与保护的dGAG缩合，合成了与大肠杆菌tRNAMetf反密码子环互补的脱氧寡核苷酸。产物(dA-T-G-A-G、d-T-A-T-G-A-G和d-T-T-A-T-G-A-G)通过阴离子交换或反相高效液相色谱法分离。
• Thuong, Nguyen Thanh; Barbier, Christine; Asseline, Ulysse, Phosphorus and Sulfur and the Related Elements, 1983, vol. 14, p. 357 - 366
  作者：Thuong, Nguyen Thanh、Barbier, Christine、Asseline, Ulysse

  DOI：——

  日期：——
• Seliger, Hartmut; Bach, Trung-Chinh; Siewert, Gerhard, Liebigs Annalen der Chemie, 1984, # 5, p. 835 - 853
  作者：Seliger, Hartmut、Bach, Trung-Chinh、Siewert, Gerhard、Boidol, Werner、Toepert, Michael、et al.

  DOI：——

  日期：——