Synthesis of rare sugars via epimerization catalyzed by tin-organic frameworks
Epimerization of readily available monosaccharides presents an atom-efficient approach to expand the portfolio of rare monosaccharides. Here, we report tin-organic frameworks (Sn-OF) as a highly selective catalyst for synthesis of rare monosaccharides, such as L-ribose, D-lyxose, D-talose, and L-qui...
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| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2025-01-01
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| Series: | Current Research in Green and Sustainable Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666086525000323 |
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| Summary: | Epimerization of readily available monosaccharides presents an atom-efficient approach to expand the portfolio of rare monosaccharides. Here, we report tin-organic frameworks (Sn-OF) as a highly selective catalyst for synthesis of rare monosaccharides, such as L-ribose, D-lyxose, D-talose, and L-quinovose, via epimerization reaction. Remarkable selectivity of 67–95 % for the epimerization products was achieved. The maximal yields obtained were 22 % for D-lyxose, 14 % for L-ribose, 15 % for D-talose, and 18 % for L-quinovose. Additionally, a correlation between the structure of the substrate and reaction rate was established, suggesting that the saccharides react in open-chain form, with the cis-orientation of OH-groups facilitating the epimerization. Moreover, it was shown that the catalyst can be reused in a second run. The catalytic epimerization results in a mixture of epimers, from which partial recovery of the substrate can be achieved through crystallization, as demonstrated for L-arabinose, D-galactose, and D-xylose. |
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| ISSN: | 2666-0865 |