[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl ethenyl carbonate | 152964-50-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: [(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl ethenyl carbonate
• CAS: 152964-50-6
• 化学式: C₁₃H₁₅N₅O₅
• 分子量: 321.293
• InChiKey: RWOBEMOHIGYUPQ-DJLDLDEBSA-N

物化性质

• 沸点：
  636.6±65.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl ethenyl carbonate 在 一水合肼 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以100%的产率得到[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl N-aminocarbamate
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Novel 3‘- and 5‘-Carbazoyl Nucleoside Derivatives. Regioselective Preparation of 3‘- and 5‘-Alkylidencarbazoyl Nucleosides

  摘要：

  A chemoenzymatic procedure is described for the synthesis of 3'- and 5'-carbazoyl nucleoside derivatives 12a,b, 13a,b, 14b,c, and 30b, and these are prepared for the first time. This process involves the regioselective enzymatic alkoxycarbonylation of nucleosides and the subsequent transformation with hydrazine into novel carbazoyl nucleoside derivatives. Taking into account previously reported data (relative to nucleoside, hydrazone, carbazate, and aryloxyphenoxypropionate derivatives), 3'-alkylidencarbazoyl 2'-deoxynucleosides 15a,b-18a,b, 5'-alkylidencarbazoyl 2'-deoxynucleosides 19a,b-22a,b, 5'-alkylidencarbazoyl ribonucleosides of uridine 23c-26c, and 5'-alkylidencarbazoyl-2',3'-isopropylideneadenosine 31b-34b emerge as interesting targets since they combine structural features found in both therapeutic nucleoside derivatives and fungicide/herbicide nucleoside analogues.

  DOI：

  10.1021/jo981062z
• 作为产物：
  描述：

  丙酮O-<(乙烯氧基)羰基>肟 、 2'-脱氧腺苷 以 四氢呋喃 为溶剂， 反应 8.0h， 以78%的产率得到[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl ethenyl carbonate
  参考文献：
  名称：

  嘌呤和嘧啶3'-氨基-3'-脱氧-和3'-氨基-2'，3'-二脱氧木糖核苷的合成。

  摘要：

  提出了获得3'-氨基木糖核苷13a，b和17a，b的一般方法。合成方案基于在核苷的3'活化位置的5'定向分子内亲核取代。进入的基团到达该位置的途径是从核苷的最受阻表面区域性和立体选择性地发生的。提出的方法学适用于核糖核苷和2'-脱氧核糖核苷，无论它们的碱基是否已硝化。

  DOI：

  10.1021/jo9606259

文献信息

• Chemo-enzymatic synthesis of 2′-deoxynucleoside urethanes
  作者：Luis F. García-Alles、Francisco Morís、Vicente Gotor

  DOI：10.1016/s0040-4039(00)73746-4

  日期：1993.9

  2′-Deoxynucleoside 5′- and 3′-(N-alkyl) carbamates were synthesized in a two step procedure, asing lipases to catalyze the first regioselective vinyloxycarbonylation step.

  以两步法合成2′-脱氧核苷5′-和3′-（N-烷基）氨基甲酸酯，用脂肪酶催化第一区域选择性乙烯基氧羰基化步骤。
• Synthesis of 5′-O-and 3′-O-nucleoside carbamates
  作者：Luis F. García-Alles、Vicente Gotor

  DOI：10.1016/0040-4020(94)00948-t

  日期：1995.1

  The two step synthesis of 5'-O- and 3'-O-(N-alkylcarbamoyl)-nucleosides is described. The key step is the enzymatic synthesis of 5'-O- or 3'-O-alkoxycarbonylnucleoside in a regioselective way. In a second aminolysis step these carbonates yield the corresponding urethanes. This methodology allows to assemble aminoalcohols and L-amino acids to 2'-deoxynucleosides.
• Chemoenzymatic Synthesis and High-Throughput Screening of an Aminoglycoside−Polyamine Library:  Identification of High-Affinity Displacers and DNA-Binding Ligands
  作者：Kaushal Rege、Shanghui Hu、James A. Moore、Jonathan S. Dordick、Steven M. Cramer

  DOI：10.1021/ja049437n

  日期：2004.10.1

  Chemoenzymatic parallel synthesis and high-throughput screening were employed to develop a multivalent aminoglycoside-polyamine library for use as high-affinity cation-exchange displacers and DNA-binding ligands. Regioselective lipase-catalyzed acylation, followed by chemical aminolysis, was used to generate vinyl carbonate and vinyl carbamate linkers, respectively, of the aminoglycosidic cores. These were further derivatized with polyamines, leading to library generation. A parallel batch-displacement assay was employed to identify the efficacy of the library candidates as potential displacers for protein purification. Using this approach, low-molecular-mass displacers with affinities higher than those previously observed have been identified. The aminoglycoside-polyamine library was also screened for DNA binding efficacy using an ethidium bromide displacement assay. These highly cationic molecules exhibited strong DNA-binding properties and may have potential for enhanced gene delivery.
• Synthesis of Purine and Pyrimidine 3‘-Amino-3‘-deoxy- and 3‘-Amino-2‘,3‘-dideoxyxylonucleosides
  作者：Luis F. García-Alles、Julia Magdalena、Vicente Gotor

  DOI：10.1021/jo9606259

  日期：1996.1.1

  A general procedure to obtain the 3'-aminoxylonucleosides 13a,b and 17a,b is presented. The synthetic scheme is based on the 5' directed intramolecular nucleophilic substitution at the 3'-activated position of the nucleoside. The approach of the incoming group to this position takes place regio- and stereoselectively from the most hindered face of the nucleoside. The methodology presented is applicable

  提出了获得3'-氨基木糖核苷13a，b和17a，b的一般方法。合成方案基于在核苷的3'活化位置的5'定向分子内亲核取代。进入的基团到达该位置的途径是从核苷的最受阻表面区域性和立体选择性地发生的。提出的方法学适用于核糖核苷和2'-脱氧核糖核苷，无论它们的碱基是否已硝化。
• Chemoenzymatic Synthesis of Novel 3‘- and 5‘-Carbazoyl Nucleoside Derivatives. Regioselective Preparation of 3‘- and 5‘-Alkylidencarbazoyl Nucleosides
  作者：Julia Magdalena、Susana Fernández、Miguel Ferrero、Vicente Gotor

  DOI：10.1021/jo981062z

  日期：1998.11.1

  A chemoenzymatic procedure is described for the synthesis of 3'- and 5'-carbazoyl nucleoside derivatives 12a,b, 13a,b, 14b,c, and 30b, and these are prepared for the first time. This process involves the regioselective enzymatic alkoxycarbonylation of nucleosides and the subsequent transformation with hydrazine into novel carbazoyl nucleoside derivatives. Taking into account previously reported data (relative to nucleoside, hydrazone, carbazate, and aryloxyphenoxypropionate derivatives), 3'-alkylidencarbazoyl 2'-deoxynucleosides 15a,b-18a,b, 5'-alkylidencarbazoyl 2'-deoxynucleosides 19a,b-22a,b, 5'-alkylidencarbazoyl ribonucleosides of uridine 23c-26c, and 5'-alkylidencarbazoyl-2',3'-isopropylideneadenosine 31b-34b emerge as interesting targets since they combine structural features found in both therapeutic nucleoside derivatives and fungicide/herbicide nucleoside analogues.