General substrates for stereoselective synthesis: utilization of D- and L-arabinose

General substrates for stereoselective synthesis: utilization of D- and L-arabinose

Soares, Fábio da Paixão; Silva, Maria Joselice e; Doboszewski, Bogdan

Abstract:

Carbohydrates are convenient chiral substrates during the stereoselective synthesis since their absolute configurations are known just like the methodologies of their functionalization. Both D- and L-arabinose are particularly interesting as the starting compounds since the same synthetic conditions can be used to obtain the enantiomeric products. Reported here are four procedures of deoxygenation at the position C3 of 5-t-butyldiphenylsilyl-1,2-O-isopropylidene-D- and –L-arabinofuranose 1 and 7, respectively, to obtain 3- deoxy-1,2-O-isopropylidene-D- and L-threopentofuranose 3 and 9, respectively, as the general substrates for further applications.

Carbohydrates are convenient chiral substrates during the stereoselective synthesis since their absolute configurations are known just like the methodologies of their functionalization. Both D- and L-arabinose are particularly interesting as the starting compounds since the same synthetic conditions can be used to obtain the enantiomeric products. Reported here are four procedures of deoxygenation at the position C3 of 5-t-butyldiphenylsilyl-1,2-O-isopropylidene-D- and –L-arabinofuranose 1 and 7, respectively, to obtain 3- deoxy-1,2-O-isopropylidene-D- and L-threopentofuranose 3 and 9, respectively, as the general substrates for further applications.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013716123531

Referências bibliográficas

• [1] 1 Soares, F.P.; Silva, M.J. e; Doboszewski, B. Carbohydr.Res. 2013,
• [2] accepted, and references therein.
• [3] 2 Doboszewski, B.; Silva, M.J. e; Nazarenko, A.; Nemykin, V.N. Acta Cryst.
• [4] E 2012, E68, 1109.

Como citar:

Soares, Fábio da Paixão; Silva, Maria Joselice e; Doboszewski, Bogdan; "General substrates for stereoselective synthesis: utilization of D- and L-arabinose", p-148-148. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013716123531