BioChem - DOS

Continuous-Flow Synthesis of (R)-Propylene Carbonate: An Important Intermediate in the Synthesis of Tenofovir

European journal of organic chemistry

Suveges, Nicolas S.; Rodriguez, Anderson A.; Diederichs, Carla C.; de Souza, Stefania P.; Leã o, Raquel A. C.; Miranda, Leandro S. M.; Horta, Bruno A. C.; Pedraza, Sé rgio F.; de Carvalho, Otavio V.; Pais, Karla C.; Terra, José H. C.; de Souza, Rodrigo O. M. A.

<P>(<I>R</I>)&#8208;Propylene carbonate is an important intermediate in the synthesis of tenofovir pro&#8208;drugs such as tenofovir alafenamide fumarate (TAF) and tenofovir diisoproyl fumarate (TDF). Independent of the pro&#8208;drug type, tenofovir presents a chiral secondary hydroxy derivative, which can be obtained directly from (<I>R</I>)&#8208;propylene carbonate. Herein, we report our chemo&#8208;enzymatic continuous&#8208;flow strategy towards (<I>R</I>)&#8208;propylene carbonate starting from a very cheap and renewable raw material, glycerol. We were able to synthesize (<I>R</I>)&#8208;propylene carbonate in seven continuous&#8208;flow steps, starting from glycerol, in good&#8208;to&#8208;excellent yields (66&ndash;93 %) and excellent selectivity (<I>E</I> > 200).</P>

2018

1434-193x

1099-0690

2018

23

pp.2931-2938

10.1002/ejoc.201800345

http://click.ndsl.kr/servlet/OpenAPIDetailView?keyValue=05787966&target=NART&cn=NART84997610

Continuous flow; Flow chemistry; Kinetic resolution; Chirality; Domino reactions; Synthesis design