N²-isobutyryl-2'-deoxy-[3']guanylic acid 4-chloro-phenyl ester 2-cyano-ethyl ester | 71002-59-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核糖核苷3'-磷酸盐
• 英文名称: N²-isobutyryl-2'-deoxy-[3']guanylic acid 4-chloro-phenyl ester 2-cyano-ethyl ester
• 英文别名: 2'-deoxy-N-(2-methyl-1-oxopropyl)-3'-guanylic acid, 4-chlorophenyl 2-cyanoethyl ester；3'-Guanylic acid, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 4-chlorophenyl 2-cyanoethyl ester；(4-chlorophenyl) 2-cyanoethyl [(2R,3S,5R)-2-(hydroxymethyl)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] phosphate
• CAS: 71002-59-0
• 化学式: C₂₃H₂₆ClN₆O₈P
• 分子量: 580.922
• InChiKey: LYIDOXCLRUKTOB-LABUEVLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  186
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N²-isobutyryl-2'-deoxy-[3']guanylic acid 4-chloro-phenyl ester 2-cyano-ethyl ester 在 1-mesitylsulfonyl-1H-tetrazole 、 三乙胺 作用下， 以 吡啶 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  Seliger, Hartmut; Bach, Trung-Chinh; Siewert, Gerhard, Liebigs Annalen der Chemie, 1984, # 5, p. 835 - 853

  摘要：

  DOI：
• 作为产物：
  描述：

  N2-异丁酰-5'-O-(4,4'-二甲氧基三苯基)-2'-脱氧鸟苷 在 N-甲基咪唑 、 苯磺酸 作用下， 以 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 2.0h， 生成 N²-isobutyryl-2'-deoxy-[3']guanylic acid 4-chloro-phenyl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Seliger, Hartmut; Bach, Trung-Chinh; Siewert, Gerhard, Liebigs Annalen der Chemie, 1984, # 5, p. 835 - 853

  摘要：

  DOI：

文献信息

• Rapid synthesis of oligodeoxynucleotides by using N-methylimidazole as a condensation catalyst. Syntheses of dodecanucleotides corresponding to complementary deoxyribonucleic acid of the tetrapeptide fragments of cholecystokinin-pancreozymin and vasoactive intestinal peptide.
  作者：TOSHIAKI WAKABAYASHI、SHINRO TACHIBANA

  DOI：10.1248/cpb.30.3951

  日期：——

  It has been found that N-methylimidazole (MeIm) activates stable condensing reagents such as 2, 4, 6-triisopropylbenzenesulfonyl-4-nitroimidazolide (TPSNI) and mesitylenesulfonyl-4-nitroimidazolide (MSNI). Fully protected trinucleotides which could serve as key intermediates were synthesized by using MeIm and TPSNI or MSNI. These trinucleotides were utilized in the syntheses of the dodecamers, dCATCCACCCCAT and dAGCCATCTGCTT, which correspond to the specific tetrapeptides of cholecystokininpancreozymin and vasoactive intestinal peptide.

  研究发现，N-甲基咪唑（MeIm）能够活化稳定的缩合剂，如2,4,6-三异丙基苯磺酰基-4-硝基咪唑化锂（TPSNI）和间三甲苯磺酰基-4-硝基咪唑化锂（MSNI）。通过使用MeIm和TPSNI或MSNI，合成了全保护的三核苷酸，这些三核苷酸可作为关键中间体。这些三核苷酸被用于合成十二聚体，dCATCCACCCCAT和dAGCCATCTGCTT，它们分别对应于胆囊收缩素-胰酶素和血管活性肠肽的特异性四肽序列。
• 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。
• Nucleosides and Nucleotides. Part 18.p-nitrobenzenesulfonyl nitroimidazole as a new condensing agent in the triester synthesis of oligonucleotides
  作者：Colin A. Leach、Felix Waldmeier、Christoph Tamm

  DOI：10.1002/hlca.19810640804

  日期：1981.12.16

  p-Nitrobenzenesulfonyl nitroimidazole (p-NBSNI) (5) has been shown to be an efficient and convenient condensing agent in the coupling of protected nucleotide fragments. Its utility has been demonstrated by a direct comparison with previously-described condensing agents in the synthesis of various di- and tetradeoxy-nucleotides.

  对硝基苯磺酰基硝基咪唑（p -NBSNI）（5）已证明是偶联受保护核苷酸片段的高效便捷的缩合剂。在各种二-和四-脱氧核苷酸的合成中，通过与前述缩合剂的直接比较已经证明了其实用性。
• Process for de-cyanoethylating blocked nucleotides
  申请人：ELI LILLY AND COMPANY

  公开号：EP0075392A1

  公开（公告）日：1983-03-30

  A process for selectively removing a β-cyanoethyl blocking group from the phosphate moiety of a nucleotide or polynucleotide, which comprises treating said nucleotide or polynucleotide with a primary amine having from 3 to 5 carbon atoms or diethylamine.

  一种从核苷酸或多核苷酸的磷酸分子中选择性地去除β-氰乙基封端基团的工艺，包括用具有 3 至 5 个碳原子的伯胺或二乙胺处理所述核苷酸或多核苷酸。
• SIMONCSITS, ANDRAS;GAL, TIBOR;RATHONYI, ZOLTAN
  作者：SIMONCSITS, ANDRAS、GAL, TIBOR、RATHONYI, ZOLTAN

  DOI：——

  日期：——