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An Improved Synthesis of Lamivudine and Emtricitabine
Author(s) -
Mandala Devender,
Watts Paul
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700052
Subject(s) - emtricitabine , lamivudine , chemistry , reagent , pyridinium , combinatorial chemistry , catalysis , trifluoromethanesulfonate , pyridine , protonation , medicinal chemistry , organic chemistry , virology , medicine , hepatitis b virus , ion , virus
An improved method was developed to prepare cis (‐)nucleosides, such as lamivudine (3TC) and emtricitabine (FTC). A solvent free reaction and catalyst free reaction was developed, with reduced reaction times to afford high yields in the preparation of the key 5‐hydroxy oxathiolane intermediate. For the acetylation, we developed a greener procedure using NaHCO 3 as the base instead of pyridine. In addition, a new reagent namely pyridinium triflate, was used for the crucial N ‐glycosidation reaction for the first time towards the synthesis of bioactive oxathiolane nucleosides 3TC and FTC.