C5 atom of D-galactopyranose as a source of chirality: preliminary results

C5 atom of D-galactopyranose as a source of chirality: preliminary results

Silva, Maria Joselice e; Silva, Paulo Roberto da; Doboszewski, Bogdan

Abstract:

Carbohydrates, terpenes and aminoacids are widely used chiral-pool substrates for stereoselective synthesis. D-Galactose is a convenient compound in this context since it is the only easily available sugar furnishing its derivative, viz. 1, which displays primary OH group in a single protecting step. We reasoned that 1 can be further extended to get 2, which upon degradation would furnish the chiral products 3. The stereogenic center present in 3 is the C5 atom in 1. The objective of this communication is to present preliminary results of such investigation.

Carbohydrates, terpenes and aminoacids are widely used chiral-pool substrates for stereoselective synthesis. D-Galactose is a convenient compound in this context since it is the only easily available sugar furnishing its derivative, viz. 1, which displays primary OH group in a single protecting step. We reasoned that 1 can be further extended to get 2, which upon degradation would furnish the chiral products 3. The stereogenic center present in 3 is the C5 atom in 1. The objective of this communication is to present preliminary results of such investigation.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013716131132

Referências bibliográficas

• [1] 1 Knauer, S.; Kranke, B.; Krause, L.; Kunz, H. Curr.Org.Chem. 2004, 8,
• [2] 1739.
• [3] 2 Liu, W. “Terpenes: The Expansion of the Chiral Pool” in “Handbook of
• [4] Chiral Chemicals”; 2nd ed.; Ager, D. Ed.; CRC Press: Boca Raton, 2005,
• [5] p.59.
• [6] 3.Williams, R.M.; Burnett, C.M. ACS Symp.Ser. 2009, 1009, 420.

Como citar:

Silva, Maria Joselice e; Silva, Paulo Roberto da; Doboszewski, Bogdan; "C5 atom of D-galactopyranose as a source of chirality: preliminary results", p-149-149. 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_2013716131132