1. Highly Stereoselective Synthesis of Lamivudine (3TC) and Emtricitabine (FTC) by a Novel N-Glycosidation Procedure
- Author
-
Stefano D'Errico, Maria Federica Caso, Giovanni Palumbo, Daniele D'Alonzo, Annalisa Guaragna, Caso, MARIA FEDERICA, D'Alonzo, Daniele, D'Errico, Stefano, Palumbo, Giovanni, and Guaragna, Annalisa
- Subjects
Glycosylation ,Silanes ,Molecular Structure ,Stereochemistry ,Medicine (all) ,Organic Chemistry ,Substrate (chemistry) ,Lamivudine ,Stereoisomerism ,Emtricitabine ,Deoxycytidine ,Biochemistry ,chemistry.chemical_compound ,chemistry ,Reagent ,Anhydrous ,medicine ,Stereoselectivity ,Physical and Theoretical Chemistry ,Cytosine ,medicine.drug - Abstract
The combined use of silanes (Et3SiH or PMHS) and I2 as novel N-glycosidation reagents for the synthesis of bioactive oxathiolane nucleosides 3TC and FTC is reported. Both systems (working as anhydrous HI sources) were devised to act as substrate activators and N-glycosidation promoters. Excellent results in terms of chemical efficiency and stereoselectivity of the reactions were obtained; surprisingly, the nature of the protective group at the N4 position of (fluoro)cytosine additionally influenced the stereochemical reaction outcome.
- Published
- 2015
- Full Text
- View/download PDF