Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5215611 | Tetrahedron | 2015 | 4 Pages |
Abstract
Amino acid esters of nucleosides at 5â²-position, as peptidomimetic prodrugs, which could be actively transported by the intestinal oligopeptide transporters 1 (PepT1), bear improved oral bioavailability. We established here a regioselective synthesis of the 5â²-esters of some nucleosides via an orthogonal protecting protocol with triphenylmethyl (Tr) and allyloxycarbonyl (AOC) protecting groups. A series of 5â²-esters of cytarabine and gemcitabine were selectively synthesized in over 36.0% total yields. This efficient and robust methodology will be examplified for the further study of the prodrugs of large number of antiviral and anticancer nucleosides.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Jia-An Liu, Xiao-Peng Guo, Shuang Liang, Fei An, Hong-Yan Shen, You-Jun Xu,