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Efficient Synthesis of UDP-Furanoses via 4,5-Dicyanoimidazole(DCI)-Promoted Coupling of Furanosyl-1-Phosphates with Uridine Phosphoropiperidate

Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang 330013, China
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Academic Editor: Katherine L. Seley-Radtke
Molecules 2019, 24(4), 655; https://doi.org/10.3390/molecules24040655
Received: 18 January 2019 / Revised: 10 February 2019 / Accepted: 11 February 2019 / Published: 13 February 2019
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Abstract

A P(V)-N activation method based on nucleoside phosphoropiperidate/DCI system has been developed for improved synthesis of diverse UDP-furanoses. The reaction conditions including temperature, amount of activator, and reaction time were optimized to alleviate the degradation of UDP-furanoses to cyclic phosphates. In addition, an efficient and facile phosphoramidite route was employed for the preparation of furanosyl-1-phosphates. View Full-Text
Keywords: NDP-sugar; P(V)-N activation; furanosyl-1-phosphate; nucleoside phosphoropiperidate; 4,5-dicyanoimidazole NDP-sugar; P(V)-N activation; furanosyl-1-phosphate; nucleoside phosphoropiperidate; 4,5-dicyanoimidazole
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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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Chen, W.-J.; Han, S.-B.; Xie, Z.-B.; Huang, H.-S.; Jiang, D.-H.; Gong, S.-S.; Sun, Q. Efficient Synthesis of UDP-Furanoses via 4,5-Dicyanoimidazole(DCI)-Promoted Coupling of Furanosyl-1-Phosphates with Uridine Phosphoropiperidate. Molecules 2019, 24, 655.

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