Synthesis of 4,5,-bis(2',3',4',6'-tetra-0-acetyl-B-D-glucopyranosylthio)-1,3-dithiole-2-thione

• Main Author: Alto, Philip Reginald Cabanos
• Format: text
• Language: English
• Published: Animo Repository 1998
• Subjects: Coordination compounds; Crown ethers; Chemical reactions; Organic compounds > Synthesis; Chemistry, Organic; Chemistry
• Online Access: https://animorepository.dlsu.edu.ph/etd_masteral/1925; https://animorepository.dlsu.edu.ph/cgi/viewcontent.cgi?article=8763&context=etd_masteral
• Institution: De La Salle University

A novel dithiole derivative containing a fully acetylated B-D-glucopyranose 3 was synthesized in 21.02 percent yield. The program of preparation involves the protection of the glucose unit via acetylation with sodium acetate in acetic anhydride at elevated temperature to produce a pentaacetylated glucopyranose 33. Subsequently, bromination in C-1' was achieved by adding HBr in acetic acid to compound 33. Finally, substitution of the acetylated glucose moiety in the 4 and 5 positions of a previously prepared zinc complex generated compound 3 through a Koennig Knorr type reaction. [Note: Diagram follows].