Gemcitabine Chemistry

Gemcitabine is a constructed pyrimidine nucleoside prodrug — a nucleoside analog in which the hydrogen atoms on the 2′ carbon of deoxycytidine are replaced by fluorine atoms.

The amalgam declared and pictured beneath is the aboriginal amalgam done in the Eli Lilly Company labs. Amalgam begins with enantiopure D-glyceraldehyde (R)-2 as the starting actual which can fabricated from D-mannitol in 2-7 steps. Then fluorine is alien by a “building block” access application ethyl bromoidfluroacetate. Then, reformatsky acknowledgment beneath accepted altitude will crop a 3:1 anti/syn diastereomeric mixture, with one above product. Separation of the diastereomers is agitated out via HPLC,thus acquiescent the anti-3 gemcitabine in a 65% yield. At atomic two added abounding amalgam methods accept aswell been developed by altered groups.