Start Date
23-4-2026 12:00 AM
Description
The continual need to develop strategies and methods for oligosaccharide synthesis drives carbohydrate chemists to discover new glycosides. This push has led to the discovery of an attractive 6-methylpyrid-2-yl leaving group for chemical glycosylation. Presented are three syntheses of the molecules 2-mercapto-6-methylpyridine, glycosyl donor 6-methylpyrid-2-yl-2,3,4,6-O-acetyl-1-thio-β-D-glucopyranoside, and glycosyl acceptor methyl-2,3,4-O-benzyl-α-D-glucopyranoside. The 2-mercapto-6-methylpyridine molecule was affixed to the requisite sugar to produce the glycosyl donor, 6-methylpyrid-2-yl-2,3,4,6-O-acetyl-1-thio-β-D-glucopyranoside. This sugar was then coupled with methyl-2,3,4-O-benzyl-α-D-glucopyranoside using silver triflate (AgOTf) to obtain the targeted disaccharide.
Research Highlights
The Problem: Carbohydrate chemistry requires the development of efficient strategies and methods for synthesizing new glycosides, specifically the formation of disaccharides through chemical glycosylation.
The Method: Researchers synthesized a glycosyl acceptor (methyl-2,3,4-O-benzyl-a-D-glucopyranoside) using triphenylmethyl chloride and benzyl bromide, a thiol leaving group (2-mercapto-6-methylpyridine) using Lawesson's Reagent, and a glycosyl donor (6-methylpyrid-2-yl-2,3,4,6-O-acetyl-1-thio-B-D-glucopyranoside) via a bromination reaction.
Quantitative Finding: The synthesis of the glycosyl acceptor achieved a 79% yield after the trityl group was cleaved with wet trifluoroacetic acid; the thiol leaving group was synthesized in 72% yield; the glycosyl donor was produced in 90% yield; the final beta-linked disaccharide was obtained with a 41% yield.
Recommended Citation
Dunn, Abby, "Complete Synthesis of a Beta-linked Disaccharide" (2026). 2026 Student Academic Showcase. 15.
https://digitalcommons.lindenwood.edu/src_2026/Posters/1/15
Included in
Complete Synthesis of a Beta-linked Disaccharide
The continual need to develop strategies and methods for oligosaccharide synthesis drives carbohydrate chemists to discover new glycosides. This push has led to the discovery of an attractive 6-methylpyrid-2-yl leaving group for chemical glycosylation. Presented are three syntheses of the molecules 2-mercapto-6-methylpyridine, glycosyl donor 6-methylpyrid-2-yl-2,3,4,6-O-acetyl-1-thio-β-D-glucopyranoside, and glycosyl acceptor methyl-2,3,4-O-benzyl-α-D-glucopyranoside. The 2-mercapto-6-methylpyridine molecule was affixed to the requisite sugar to produce the glycosyl donor, 6-methylpyrid-2-yl-2,3,4,6-O-acetyl-1-thio-β-D-glucopyranoside. This sugar was then coupled with methyl-2,3,4-O-benzyl-α-D-glucopyranoside using silver triflate (AgOTf) to obtain the targeted disaccharide.