Towards chiral 1,2-propanediols via desymmetrization

Towards chiral 1,2-propanediols via desymmetrization

Siqueira, Edmilson Clarindo de; Doboszewski, Bogdan

Abstract:

General tendency in the pharmaceutical industry is to use either a chiral substrates or to perform chiral separations to obtain only one specific isomer as an active principle in order to decrease a metabolic load in patient´s organism. Tenofovir 1 is an active principle of the Viraed® and is liberated from its prodrug form. Viraed® is approved for treatment of HIV and HBV infections as an inhibitor of reversed transcriptase. One of the components of Tenofovir is (R)- 1,2-propanediol 2. Reported here are initial stages of obtention of (R) 2 and its enantiomer (S) 2 via desymmetrization of easily available glycerol and racemic 1,2-propanediol.

General tendency in the pharmaceutical industry is to use either a chiral substrates or to perform chiral separations to obtain only one specific isomer as an active principle in order to decrease a metabolic load in patient´s organism. Tenofovir 1 is an active principle of the Viraed® and is liberated from its prodrug form. Viraed® is approved for treatment of HIV and HBV infections as an inhibitor of reversed transcriptase. One of the components of Tenofovir is (R)- 1,2-propanediol 2. Reported here are initial stages of obtention of (R) 2 and its enantiomer (S) 2 via desymmetrization of easily available glycerol and racemic 1,2-propanediol.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0023-1

Referências bibliográficas

• [1] 1 Norula, J.L. Chemical Era, 1975, 11, 21.
• [2] 2 Pallavicini, M.; Valoti, E.; Villa, L.; Piccolo, O. Tetrahedron: Asymmetry, 1994, 5, 5.2 Sterochemistry of Organic Compounds. Eliel, E.L.; Wilen, S.H.; Mander, L.N. John Wiley and Sons, New York, 1994.

Como citar:

Siqueira, Edmilson Clarindo de; Doboszewski, Bogdan; "Towards chiral 1,2-propanediols via desymmetrization", p-23-23. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0023-1