引用本文:
夏然, 孙莉萍, 杨西宁, 渠桂荣. 无金属催化合成2,6-二氯嘌呤核苷和2-氯腺苷[J]. 应用化学,
2015, 32(12): 1398-1401.
doi:
10.11944/j.issn.1000-0518.2015.12.150232
Citation: XIA Ran, SUN Liping, YANG Xining, QU Guirong. Metal-free Synthesis of 2,6-Dichloropurineside and 2-Chloroadenosine[J]. Chinese Journal of Applied Chemistry, 2015, 32(12): 1398-1401. doi: 10.11944/j.issn.1000-0518.2015.12.150232
Citation: XIA Ran, SUN Liping, YANG Xining, QU Guirong. Metal-free Synthesis of 2,6-Dichloropurineside and 2-Chloroadenosine[J]. Chinese Journal of Applied Chemistry, 2015, 32(12): 1398-1401. doi: 10.11944/j.issn.1000-0518.2015.12.150232
无金属催化合成2,6-二氯嘌呤核苷和2-氯腺苷
English
Metal-free Synthesis of 2,6-Dichloropurineside and 2-Chloroadenosine
Abstract:
New methods for the synthesis of 2,6-dichloropurineside and 2-chloroadenosine were developed.The key intermediate 2',3',5'-tri-O-acetyl-2,6-dichloropurineside was obtained from the condensation of 2,6-dichloropurine and β-D-ribofuranose 1,2,3,5-tetraacetate under the catalysis of 5% molar fraction of trifluoromethanesulfonic acid. 2,6-Dichloropurineside was obtained by sulfuric acid catalyzed hydrolysis of 2',3',5'-tri-O-acetyl-2,6-dichloropurineside in the yield of 89% and 2-chloroadenosine was obtained from the aminolysis of 2',3',5'-tri-O-acetyl-2,6-dichloropurineside in NH3/CH3OH with the yield of 92%. The starting substrates were all commercially available and affordable. The presented method avoided toxic metal catalysts and chromatography. Moreover,2-thioadenosine was obtained in reliable yield on a 100 g scale.
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Key words:
- dichloropurineside
- / chloroadenosine
- / metal-free
- / dichloropurine
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