Citation: SUN Liping, XIA Ran. Synthesis of α-Adenine Arabinoside under Solvent-and Catalyst-Free Conditions[J]. Chinese Journal of Applied Chemistry, ;2019, 36(3): 300-305. doi: 10.11944/j.issn.1000-0518.2019.03.180200 shu

Synthesis of α-Adenine Arabinoside under Solvent-and Catalyst-Free Conditions

SUN Liping ^a ,
XIA Ran ^b,,

a.
School of Life Science and Technology, Xinxiang University, Xinxiang, He'nan 453003, China
b.
College of Chemistry and Chemical Engineering, Xinxiang University, Xinxiang, He'nan 453003, China

Corresponding author: XIA Ran, ranxia518@hotmail.com
Received Date: 29 May 2018
Revised Date: 31 July 2018
Accepted Date: 29 August 2018

Fund Project: Supported by the National Natural Science Foundation of China(No.21602189), the Development Project for Science and Technology of He′nan Province(No.172102310212, No.172102310213), the Key Research Projects for University of He′nan Province(No.16A150042, No.16A180035)the National Natural Science Foundation of China 21602189the Key Research Projects for University of He′nan Province 16A180035the Key Research Projects for University of He′nan Province 16A150042the Development Project for Science and Technology of He′nan Province 172102310212the Development Project for Science and Technology of He′nan Province 172102310213

Figures(4)

In order to develop the efficient synthesis of α-adenine arabinoside, the key intermediate 9-α-D-(2', 3', 5'-tri-O-acetyl)-6-chloropurineside was obtained in 85% yield from the condensation of 6-chloropurine and 1, 2, 3, 5-tetra-O-acetatyl-β-D-arabinose under solvent-and catalyst-free conditions with microwave irradiation. α-Adenine arabinoside was synthesized from the intermediate via deacetylation catalyzed by Na₂CO₃, followed by aminolysis in saturated NH₃/CH₃OH in one pot. The intermediate was obtained in consist yield even on a 100 g scale. The analogues α-2-fluoroadenine arabinoside and α-2-aminoadenine arabinoside were obtained via similar method.
- α-adenine arabinoside,
- solvent-free,
- microwave irradiation,
- metal-free
1. [1]
  Theobald R J. Vidarabine[M]. 2016, Elsevier Inc.
2. [2]
  Revankar G R, Huffman J H, Allen L B. Synthesis and Antiviral Activity of Certain 5'-Monophosphates of 9-D-Arabinofuranosyladenine and 9-D-Arabinofuranosylhypoxanthine[J]. J Med Chem, 1975,18(7):721-726. doi: 10.1021/jm00241a016
3. [3]
  Thomas H J, Montgomery J A. 7-Glycosylpurines.Ⅱ.Arabinofuranosides of Hypoxanthine and Adenine[J]. J Org Chem, 1966,31(5):1413-1416. doi: 10.1021/jo01343a023
4. [4]
  York J L. Effect of the Structure of the Glycon on the Acid-catalyzed Hydrolysis of Adenine Nucleosides[J]. J Org Chem, 1981,46(10):2171-2173. doi: 10.1021/jo00323a040
5. [5]
  Lee W W, Benitez A, Goodman L. Potential Anticancer Agent:Synthesis of the β-Anomer of 9-(D-Arabinofuranosyl) Adenine[J]. J Am Chem Soc, 1960,82(10):2648-2649. doi: 10.1021/ja01495a070
6. [6]
  Bookser B C, Raffaele N B. High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries[J]. J Org Chem, 2007,72(1):173-179.
7. [7]
  Qu G R, Han S H, Zhang Z G. Microwave-assisted Regioselective Synthesis of Acyclic Nucleosides Through an Alkylating Reaction with 2-Axa-1, 4-butanediol Diacetate[J]. Can J Chem, 2006,84(5):819-824. doi: 10.1139/v06-061
8. [8]
  Montgomery J A, Laseter A G, Shortnacy A T. Nucleosides of 2-Azapurines. 7H-Imidazo[4, 5-d]-1, 2, 3-triazines[J]. J Med Chem, 1975,18(6):564-567. doi: 10.1021/jm00240a006
9. [9]
  Janeba Z, Francom P, Robins M J. Efficient Syntheses of 2-Chloro-2-deoxyadenosine(Cladribine) from 2-Deoxyguanosine[J]. J Org Chem, 2003,68(3):989-992. doi: 10.1021/jo020644k
1. [1]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
2. [2]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
3. [3]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
4. [4]
  Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024
5. [5]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
6. [6]
  Dan Li , Hui Xin , Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046
7. [7]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
8. [8]
  Juan WANG , Zhongqiu WANG , Qin SHANG , Guohong WANG , Jinmao LI . NiS and Pt as dual co-catalysts for the enhanced photocatalytic H₂ production activity of BaTiO₃ nanofibers. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1719-1730. doi: 10.11862/CJIC.20240102
9. [9]
  Yang WANG , Xiaoqin ZHENG , Yang LIU , Kai ZHANG , Jiahui KOU , Linbing SUN . Mn single-atom catalysts based on confined space: Fabrication and the electrocatalytic oxygen evolution reaction performance. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2175-2185. doi: 10.11862/CJIC.20240165
10. [10]
  Wen YANG , Didi WANG , Ziyi HUANG , Yaping ZHOU , Yanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO₂ methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276
11. [11]
  Asif Hassan Raza , Shumail Farhan , Zhixian Yu , Yan Wu . 用于高效制氢的双S型ZnS/ZnO/CdS异质结构光催化剂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406020-. doi: 10.3866/PKU.WHXB202406020
12. [12]
  Qingqing SHEN , Xiangbowen DU , Kaicheng QIAN , Zhikang JIN , Zheng FANG , Tong WEI , Renhong LI . Self-supporting Cu/α-FeOOH/foam nickel composite catalyst for efficient hydrogen production by coupling methanol oxidation and water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1953-1964. doi: 10.11862/CJIC.20240028
13. [13]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
14. [14]
  Shuang Yang , Qun Wang , Caiqin Miao , Ziqi Geng , Xinran Li , Yang Li , Xiaohong Wu . Ideological and Political Education Design for Research-Oriented Experimental Course of Highly Efficient Hydrogen Production from Water Electrolysis in Aerospace Perspective. University Chemistry, 2024, 39(11): 269-277. doi: 10.12461/PKU.DXHX202403044
15. [15]
  Yulian Hu , Xin Zhou , Xiaojun Han . A Virtual Simulation Experiment on the Design and Property Analysis of CO₂ Reduction Photocatalyst. University Chemistry, 2025, 40(3): 30-35. doi: 10.12461/PKU.DXHX202403088
16. [16]
  Xue Liu , Lipeng Wang , Luling Li , Kai Wang , Wenju Liu , Biao Hu , Daofan Cao , Fenghao Jiang , Junguo Li , Ke Liu . Cu基和Pt基甲醇水蒸气重整制氢催化剂研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100049-. doi: 10.1016/j.actphy.2025.100049
17. [17]
  Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO₂ cycloaddition over W₁₈O₄₉/NH₂-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
18. [18]
  Yi YANG , Shuang WANG , Wendan WANG , Limiao CHEN . Photocatalytic CO₂ reduction performance of Z-scheme Ag-Cu₂O/BiVO₄ photocatalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 895-906. doi: 10.11862/CJIC.20230434
19. [19]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081
20. [20]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(504)
HTML views(63)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142