Ru-catalysed stereoselective glycosylation of C-2 substituted glycals: an efficient route to 3-deoxy-1,2-difunctionalized pseudoglycals

The stereoselective formation of glycosidic bonds remains a key challenge in carbohydrate chemistry, with far-reaching implications for glycoscience, drug development, and materials research. We report a novel method for glycosylation of glycal-derived substrates mediated by Ru(II) catalysis. Glycosylation selectivity is modulated by the presence or absence of external nucleophiles in the reaction medium. This transformation is notable for its operational simplicity, scalability, and use of cost-effective, air-stable Ru(II) catalysts. Notably, the reaction exhibits exceptional β-selectivity, offering an efficient and streamlined approach for synthesising 3-deoxy-1,2-difunctionalized glycals.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob01261a
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
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article

Ru-catalysed stereoselective glycosylation of C-2 substituted glycals: an efficient route to 3-deoxy-1,2-difunctionalized pseudoglycals

Ram Pratap Pandey, Nazar Hussain, Manish Sharma, Bindu Tiwari
Organic & Biomolecular Chemistry
Carbohydrate Chemistry and Synthesis
article

Ru-catalysed stereoselective glycosylation of C-2 substituted glycals: an efficient route to 3-deoxy-1,2-difunctionalized pseudoglycals

Ram Pratap Pandey, Nazar Hussain, Manish Sharma, Bindu Tiwari
article en

Abstract

The stereoselective formation of glycosidic bonds remains a key challenge in carbohydrate chemistry, with far-reaching implications for glycoscience, drug development, and materials research. We report a novel method for glycosylation of glycal-derived substrates mediated by Ru(II) catalysis. Glycosylation selectivity is modulated by the presence or absence of external nucleophiles in the reaction medium. This transformation is notable for its operational simplicity, scalability, and use of cost-effective, air-stable Ru(II) catalysts. Notably, the reaction exhibits exceptional β-selectivity, offering an efficient and streamlined approach for synthesising 3-deoxy-1,2-difunctionalized glycals.

Organic & Biomolecular ChemistryVol. 23(37)
Institute of Medical Sciences (IN), Banaras Hindu University (IN)
Openalex Percentile: Top 83%
Carbohydrate Chemistry and Synthesis
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Ru-catalysed stereoselective glycosylation of C-2 substituted glycals: an efficient route to 3-deoxy-1,2-difunctionalized pseudoglycals — Ram Pratap Pandey, Nazar Hussain, et al. · Organic & Biomolecular Chemistry (2025) | TGRS Research Map | TGRS