2-chloro-2'deoxyadenosine | 114128-13-1

• 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: 2-chloro-2'deoxyadenosine
• 英文别名: 2-Chlor-2'-desoxyadenosin；(2R,3S)-5-(6-amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 114128-13-1
• 化学式: C₁₀H₁₂ClN₅O₃
• 分子量: 285.69
• InChiKey: PTOAARAWEBMLNO-YRZWDFBDSA-N

物化性质

• 沸点：
  597.6±60.0 °C(Predicted)
• 密度：
  2.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-chloro-6-(4-N,N-dimethylaminopyridin-1-yl)-[2′-deoxy-3′,5′-di-O-(p-toluoyl)-α/β-D-erythro-pentofuranosyl]purine chloride 在 氨 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-chloro-2'deoxyadenosine
  参考文献：
  名称：

  Selective Preparations of Purine Nucleosides and Nucleotides: Reagents and Methods

  摘要：

  描述了一种在溶液或固相合成中合成N-9嘌呤核苷类似物的位置特异性合成过程。将糖基或其类似物引入到6-杂环嘌呤或其共振甲基盐上，从而仅形成嘌呤核苷类似物的N-9位置异构体（D或L对映体）。这种糖基的位置特异性引入允许在高产率下合成嘌呤核苷类似物，而不形成N-7位置异构体，而6-杂环嘌呤是易于亲核置换的离去基团。固相支持的6-杂环嘌呤碱可以用于嘌呤基库合成和核苷酸一磷酸和多磷酸的合成。描述了提供新颖的6-杂环嘌呤及其相应的共振甲基盐以用于N-9嘌呤核苷类似物和核苷酸的位置特异性合成的过程。

  公开号：

  US20150376219A1

文献信息

• [EN] METHOD FOR PRODUCING 2'-DEOXYADENOSINE COMPOUNDS<br/>[FR] PROCÉDÉ DE PRODUCTION DE COMPOSÉS DE 2'-DÉSOXYADÉNOSINE
  申请人：CILAG AG

  公开号：WO2011113476A2

  公开（公告）日：2011-09-22

  (A) reacting the alkali metal salt of 2, 6-dichlorpurine with a 2-desoxy-3, 5 -di-O-p-toluoyl-alpha-D-erythro-pentofuranose or a derivative thereof, in a suitable organic solvent, said reaction optionally being carried out in the presence of a Lewis-acid, whereby a mixture comprising the intermediate N (9) -beta-compound, the N (7) -beta-regio- isomer, and the N (9) -alpha-stereoisomer is formed; (B) isolating from said reaction mixture formed the crude reaction product comprising the intermediate N (9) -beta- compound by a purification method, preferably by precipitation or crystallization, using a suitable organic solvent or a mixture of such organic solvents or a mixture of one or more of such organic solvents with water, without using a chromatographic purification method, and (C) subjecting the isolated intermediate N (9 ) -beta-compound to ammonolysis, where upon the 2 '-deoxyadenosine compound is formed, and (D) precipitating or crystallizing the 2 '-deoxyadenosine compound as formed in step (C) from a suitable organic solvent.

  (A) 使2,6-二氯嘌呤的碱金属盐与2-去氧-3,5-二-O-p-甲苯酰基-α-D-赤 trựcофuranose或其衍生物在合适的有机溶剂中反应，该反应可选在路易斯酸存在下进行，从而形成包含中间体N(9)-β化合物、N(7)-β区域异构体和N(9)-α旋光异构体的混合物； (B) 通过净化方法（优选为沉淀或结晶）从上述反应混合物中分离出包含中间体N(9)-β化合物的粗反应产物，使用合适的有机溶剂或多种此类有机溶剂的混合物，或一种或多种此类有机溶剂与水的混合物，且不使用色谱净化方法； (C) 将分离得到的中间体N(9)-β化合物进行氨解，从而生成2’-去氧腺苷化合物；以及 (D) 将步骤(C)中生成的2’-去氧腺苷化合物从合适的有机溶剂中沉淀或结晶。
• POSITRON EMISSION TOMOGRAPHY PROBES FOR IMAGING IMMUNE ACTIVATION AND SELECTED CANCERS
  申请人：Radu Caius G.

  公开号：US20090105184A1

  公开（公告）日：2009-04-23

  Compounds for use as PET probes and methods for synthesizing and using these, comprising [ 18 F]D-FAC and other cytosine and adenosine analogs.
• US8101740B2
  申请人：——

  公开号：US8101740B2

  公开（公告）日：2012-01-24
• Selective Preparations of Purine Nucleosides and Nucleotides: Reagents and Methods
  申请人：Zhong Minghong

  公开号：US20150376219A1

  公开（公告）日：2015-12-31

  A process of regiospecific synthesis of N-9 purine nucleoside analogs in either solution or solid phase synthesis is described. The introduction of the sugar moiety or its analogue on to a 6-heteroarylium purine or its mesomeric betaine so that formation of only the N-9 position regioisomers of the purine nucleoside analogs (either D or L enantiomers) is obtained. This regiospecific introduction of the sugar moiety allows the synthesis of purine nucleoside analogs in high yields without formation of the N-7-positional regioisomers, while the 6-heteroaryliums are leaving groups facilitated for nucleophilic displacement. Solid supported 6-heterarylium purine bases can be used for purine based library synthesis and synthesis of nucleotide monophosphates and polyphosphates. Processes for providing novel 6-heteroarylium purines and their corresponding mesomeric betaines for the regiospecific synthesis of N-9 purine nucleoside analogs and nucleotides are described.

  描述了一种在溶液或固相合成中合成N-9嘌呤核苷类似物的位置特异性合成过程。将糖基或其类似物引入到6-杂环嘌呤或其共振甲基盐上，从而仅形成嘌呤核苷类似物的N-9位置异构体（D或L对映体）。这种糖基的位置特异性引入允许在高产率下合成嘌呤核苷类似物，而不形成N-7位置异构体，而6-杂环嘌呤是易于亲核置换的离去基团。固相支持的6-杂环嘌呤碱可以用于嘌呤基库合成和核苷酸一磷酸和多磷酸的合成。描述了提供新颖的6-杂环嘌呤及其相应的共振甲基盐以用于N-9嘌呤核苷类似物和核苷酸的位置特异性合成的过程。