Carbonic acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester vinyl ester | 152964-51-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Carbonic acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester vinyl ester
• 英文别名: [(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] ethenyl carbonate
• CAS: 152964-51-7
• 化学式: C₁₃H₁₅N₅O₅
• 分子量: 321.293
• InChiKey: ARQOIGFHNZCMSU-DJLDLDEBSA-N

物化性质

• 沸点：
  618.2±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)：
  0.5
• 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：

  Carbonic acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester vinyl ester 在 一水合肼 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以100%的产率得到[(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] 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 在 PS lipase 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到Carbonic acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester vinyl ester
  参考文献：
  名称：

  化学酶法合成2'-脱氧核苷氨基甲酸酯

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)73746-4

文献信息

• 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 novel carbazoyl linked pyrimidine-pyrimidine and pyrimidine-purine dinucleotide analogues
  作者：Julia Magdalena、Susana Fernández、Miguel Ferrero、Vicente Gotor

  DOI：10.1016/s0040-4039(99)00009-x

  日期：1999.2

  The synthesis of two backbone modified dinucleotide analogues is described in which the natural phosphodiester linkage is replaced by a 3'-5' carbazoyl linkage. In both cases the bridge was formed through a coupling reaction between an appropriate 3'-carbazoyl nucleoside analogue and an aldehyde nucleoside derivative. It is noteworthy that starting nucleosides 4 could be common materials to obtain the 3'-carbazoyl nucleoside derivatives 2, by means of a simple, previously-described chemoenzymatic procedure, and the aldehyde nucleoside 3, by an oxidation reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.