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An Expeditious Total Synthesis of 5′-Deoxy-toyocamycin and 5′-Deoxysangivamycin

Key Laboratory of Organic Chemistry in Jiangxi Province, Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, China
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Academic Editors: Katherine L. Seley-Radtke and Theodore K. Dayie
Molecules 2019, 24(4), 737; https://doi.org/10.3390/molecules24040737
Received: 4 February 2019 / Revised: 15 February 2019 / Accepted: 16 February 2019 / Published: 19 February 2019
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Abstract

In present paper, an expeditious total synthesis of naturally occurring 5′-deoxytoyocamycin and 5′-deoxysangivamycin was accomplished. Because of the introduction of a benzoyl group at N-6 of 4-amino-5-cyano-6-bromo-pyrrolo[2,3-d]pyrimidine, a Vorbrüggen glycosylation with 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose afforded a completely regioselective N-9 glycosylation product, which is unambiguously confirmed by X-ray diffraction analysis. All of the involved intermediates were well characterized by various spectra. View Full-Text
Keywords: nucleoside; 7-deazapurine; pyrrolo[2,3-d]pyrimidine; total synthesis nucleoside; 7-deazapurine; pyrrolo[2,3-d]pyrimidine; total synthesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Dong, X.; Tang, J.; Hu, C.; Bai, J.; Ding, H.; Xiao, Q. An Expeditious Total Synthesis of 5′-Deoxy-toyocamycin and 5′-Deoxysangivamycin. Molecules 2019, 24, 737.

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