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Molecules. 2019 Feb 13;24(4). pii: E655. doi: 10.3390/molecules24040655.

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

Author information

1
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang 330013, China. chenweijie9@126.com.
2
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang 330013, China. hanshuaibo1@126.com.
3
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang 330013, China. xiezhenbiao1@126.com.
4
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang 330013, China. huanghuashan1@126.com.
5
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang 330013, China. jiangduohua@126.com.
6
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang 330013, China. gongshanshan@jxstnu.edu.cn.
7
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang 330013, China. sunqi@jxstnu.edu.cn.

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.

KEYWORDS:

4,5-dicyanoimidazole; NDP-sugar; P(V)-N activation; furanosyl-1-phosphate; nucleoside phosphoropiperidate

PMID:
30781738
PMCID:
PMC6412210
DOI:
10.3390/molecules24040655
[Indexed for MEDLINE]
Free PMC Article

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