ArticleNature communications2020
Diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols via chirality transfer from a glycosyl donor.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 42 citations in OpenAlex.
- A universal O-glycosylation platform enabled by pyridinium catalysis using gas-releasing oxazolidinone-based carbamates donors.Nature communications · 2025Article
- Total Synthesis of Kanamycins.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Stereoselective Total Synthesis of α-Galacto-Oligosaccharides Using Boron-Mediated Aglycon Delivery and Evaluation of their Immune-Enhancing Activities.Chembiochem : a European journal of chemical biology · 2025Article
- Creation of a macrolide antibiotic against non-tuberculousScience advances · 2025Article
- A synergistic Rh(I)/organoboron-catalysed site-selective carbohydrate functionalization that involves multiple stereocontrol.Nature chemistry · 2023Article
- Recent Chemical and Chemoenzymatic Strategies to Complex-TypeFrontiers in chemistry · 2022Review
- Recent advances in stereoselective 1,2-Frontiers in chemistry · 2022Review
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Authors and funding
8 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Chemical desymmetrization reactions of meso-diols are highly effective for the precise and efficient synthesis of chiral molecules. However, even though enzyme-catalyzed desymmetric glycosylations are frequently found in nature, there is no method for highly diastereoselective desymmetric chemical glycosylation of meso-diols. Herein, we report a highly diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols found in myo-inositol 1,3,5-orthoesters using a boronic acid catalyst based on predictions of regioselectivity by density functional theory (DFT) calculations. The enantiotopic hydroxyl groups of the meso-diols are clearly differentiated by the stereochemistry at the C2 position of the glycosyl donor with excellent regioselectivities. In addition, the present method is successfully applied to the synthesis of core structures of phosphatidylinositolmannosides (PIMs) and glycosylphosphatidylinositol (GPI) anchors, and common β-mannoside structures of the LLBM-782 series of antibiotics.
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