A Synthetic Approach of D-Glucose Derivatives: Spectral Characterization and Antimicrobial Studies

Sarkar Kawsar, Jannatul Ferdous, Golam Mostafa and Mohammad Manchur

A new series of methyl 4,6-O-(4-methoxybenzylidene)--D-glucopyranoside derivatives was synthesized using the direct acylation method. Methyl--D-glucopyranoside was selectively converted to methyl 4,6-O-(4-methoxybenzylidene)--D-glucopyranoside by the reaction with 4-methoxybenzaldehyde dimethylacetal in a reasonable yield. Using a wide variety of acylating agents, a series of 2,3-di-O-acyl derivatives of this product was also prepared in order to gather additional information for structure elucidation. The structures of the newly synthesized compounds were elucidated by their spectral and elemental analysis. All synthesized compounds were screened for in vitro antimicrobial activities against ten human pathogenic bacteria and four plant pathogenic fungi. Encouragingly, a number of test compounds showed better antimicrobial activity than the standard antibiotics employed. It observed that the test compounds were more effective against fungal phytopathogens than those of the bacterial organisms.

[1] Singh H., Shukla K., Dwivedi R. et al.: J. Agric. Food Chem., 1990, 38, 1483.
[2] Rjabova J., Rjabovs V., Moreno A. et al.: Cent. Eur. J. Chem., 2012, 10, 386.
[3] Tagashira M., Tanaka A., Hisatani K. et al.: Glycoconjugate J., 2001, 18, 449.
[4] Andry C., Wylde R., Laffite C. et al.: Phytochemistry, 1982, 21, 1123.
[5] Ishii H., Nakamura M., Seo S. et al.: Chem. Pharm. Bull., 1980, 28, 2367.