Synthesis of benzyl 6-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside and of 2-O-α-L-fucopyranosyl-D-galactose

Add time:09/09/2019    Source:sciencedirect.com

Benzyl β-D-galactopyranoside was converted into the crystalline 3,4-O-isopropylidene derivative (2), which was selectively benzoylated to give crystalline benzyl 6-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside (8. The structure of 8 was established by various reactions, which included the preparation of benzyl 6-O-benzoyl-β-D-galactopyranoside (9) and of benzyl 2-O-benzoyl-β-D-galactopyranoside (10). Condensation of 8 with 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide, followed by removal of the isopropylidene benzoyl and acetate groups, afforded crystalline benzyl 2-O-α-L-fucopyranosyl-β-D-galactopyranoside (12). Catalytic hydrogenolysis of 12 gave the disaccharide 2-O-α-L-fucopyranosyl-D-galactose (1), which was identical with the natural product.

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