Stereoselective synthesis of 2-deoxy-2-bromo-hexopyrano-β-nucleosides: solvent-free Lewis acid catalysis
Norein Sakander1,2, Qazi Naveed Ahmed1,2
1Natural Product and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu-180001, India. naqazi@iiim.ac.in.
Abstract:
An expedient solvent-free synthesis of 2-deoxy-2-bromo-hexopyrano-β-nucleosides stereo- and regioselectively from protected glycals and unactivated nucleobases using cheaper and easily available reagent systems has been developed. The synthesis is mediated by a Lewis acid and is solvent-free. The substrate scope of the reaction was analysed with ether, ester and silyl-protected glycals as donors and different pyrimidine and purine bases were taken into consideration. This method further finds application in the synthesis of 2-deoxynucleosides.
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