Polysaccharide

Modular design

Organic chemistry

Combinatorial chemistry

Glycosylation

Reagent

Stereochemistry

Operating system

Chemical synthesis

One-pot synthesis

Catalysis

Chemistry

In vitro

Computer science

Biochemistry

Angewandte Chemie International Edition

The synthesis of long, branched, and complex carbohydrate sequences remains a challenging task in chemical synthesis. Reported here is an efficient and modular one-pot synthesis of a nona-decasaccharide and shorter sequences from Psidium guajava polysaccharides, which have the potent α-glucosidase inhibitory activity. The synthetic strategy features: 1) several one-pot glycosylation reactions on the basis of N-phenyltrifluoroacetimidate (PTFAI) and Yu glycosylation to streamline the chemical synthesis of oligosaccharides, 2) the successful and efficient assembly sequences (first O3', second O5', final O2') toward the challenging 2,3,5-branched Araf motif, 3) the stereoselective 1,2-cis-glucosylation by reagent control, and 4) the convergent [6+6+7] one-pot coupling reaction for the final assembly of the target nona-decasaccharide. This orthogonal one-pot glycosylation strategy can streamline the chemical synthesis of long, branched, and complicated carbohydrate chains.

Modular Synthesis of Nona‐Decasaccharide Motif from <i>Psidium guajava</i> Polysaccharides: Orthogonal One‐Pot Glycosylation Strategy

Modular Synthesis of Nona‐Decasaccharide Motif from Psidium guajava Polysaccharides: Orthogonal One‐Pot Glycosylation Strategy