Cordyceps, Caterpillar Fungus · 2023 · Research Support, Non U.S. Gov'T
Medium relevanceModular and Stereoselective One-Pot Total Synthesis of Icosasaccharide Motif from Cordyceps sinensis EPS-1A Glycan.
Ophiocordyceps sinensis
Key points
- The first stereoselective one-pot synthesis of the icosasaccharide motif of EPS-1A glycan from Cordyceps sinensis has been achieved
- The synthetic approach highlights the following features: (1) merging reagent modulation and remote anchimeric assistance α-glycosylation strategy for the highly stereoselective formation of five and ten continuous 1,2- cis glucosidic bonds; (2) the strategic employment of glycosyl N -phenyltrifluoroacetimidates and glycosyl o -(1-phenylvinyl)benzoates as the matched pair for efficient orthogonal one-pot synthesis; and (3) [11 + 8 + 1] orthogonal one-pot glycosylation for the efficient assembly of the target icosasaccharide
Metadata-grounded summary
Citation abstract
The first stereoselective one-pot synthesis of the icosasaccharide motif of EPS-1A glycan from Cordyceps sinensis has been achieved. The synthetic approach highlights the following features: (1) merging reagent modulation and remote anchimeric assistance α-glycosylation strategy for the highly stereoselective formation of five and ten continuous 1,2- cis glucosidic bonds; (2) the strategic employment of glycosyl N -phenyltrifluoroacetimidates and glycosyl o -(1-phenylvinyl)benzoates as the matched pair for efficient orthogonal one-pot synthesis; and (3) [11 + 8 + 1] orthogonal one-pot glycosylation for the efficient assembly of the target icosasaccharide.
Citation
Sun X, Chen Z, Yang R, Wang M, Wang X, Zhang Q, et al. (2023). Modular and Stereoselective One-Pot Total Synthesis of Icosasaccharide Motif from Cordyceps sinensis EPS-1A Glycan. Organic letters https://doi.org/10.1021/acs.orglett.3c02842 PMID: 37787453
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