Green synthesis of 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol from natural d-sugars over Au/Al(2)O(3) and SO(4)(2−)/Al(2)O(3) catalysts

A green synthetic route for the synthesis of some potential enzyme active hydroxypiperidine iminosugars including 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol, starting from commercially available d-ribose and d-lyxose was tested out. Heterogeneous catalysts including Au/Al(...

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Autores principales: Gao, Hongjian, Fan, Ao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8376872/
https://www.ncbi.nlm.nih.gov/pubmed/34413372
http://dx.doi.org/10.1038/s41598-021-96231-9
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author Gao, Hongjian
Fan, Ao
author_facet Gao, Hongjian
Fan, Ao
author_sort Gao, Hongjian
collection PubMed
description A green synthetic route for the synthesis of some potential enzyme active hydroxypiperidine iminosugars including 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol, starting from commercially available d-ribose and d-lyxose was tested out. Heterogeneous catalysts including Au/Al(2)O(3), SO(4)(2−)/Al(2)O(3) as well as environmentally friendly reagents were employed into several critical reaction of the route. The synthetic route resulted in good overall yields of 1,5-dideoxy-1,5-imino-ribitol of 54%, 1,5-dideoxy-1,5-imino-d-arabinitol of 48% and 1,5-dideoxy-1,5-imino-l-arabinitol of 46%. The Au/Al(2)O(3) catalyst can be easily recovered from the reaction mixture and reused with no loss of activity.
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spelling pubmed-83768722021-08-20 Green synthesis of 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol from natural d-sugars over Au/Al(2)O(3) and SO(4)(2−)/Al(2)O(3) catalysts Gao, Hongjian Fan, Ao Sci Rep Article A green synthetic route for the synthesis of some potential enzyme active hydroxypiperidine iminosugars including 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol, starting from commercially available d-ribose and d-lyxose was tested out. Heterogeneous catalysts including Au/Al(2)O(3), SO(4)(2−)/Al(2)O(3) as well as environmentally friendly reagents were employed into several critical reaction of the route. The synthetic route resulted in good overall yields of 1,5-dideoxy-1,5-imino-ribitol of 54%, 1,5-dideoxy-1,5-imino-d-arabinitol of 48% and 1,5-dideoxy-1,5-imino-l-arabinitol of 46%. The Au/Al(2)O(3) catalyst can be easily recovered from the reaction mixture and reused with no loss of activity. Nature Publishing Group UK 2021-08-19 /pmc/articles/PMC8376872/ /pubmed/34413372 http://dx.doi.org/10.1038/s41598-021-96231-9 Text en © The Author(s) 2021 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Gao, Hongjian
Fan, Ao
Green synthesis of 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol from natural d-sugars over Au/Al(2)O(3) and SO(4)(2−)/Al(2)O(3) catalysts
title Green synthesis of 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol from natural d-sugars over Au/Al(2)O(3) and SO(4)(2−)/Al(2)O(3) catalysts
title_full Green synthesis of 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol from natural d-sugars over Au/Al(2)O(3) and SO(4)(2−)/Al(2)O(3) catalysts
title_fullStr Green synthesis of 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol from natural d-sugars over Au/Al(2)O(3) and SO(4)(2−)/Al(2)O(3) catalysts
title_full_unstemmed Green synthesis of 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol from natural d-sugars over Au/Al(2)O(3) and SO(4)(2−)/Al(2)O(3) catalysts
title_short Green synthesis of 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol from natural d-sugars over Au/Al(2)O(3) and SO(4)(2−)/Al(2)O(3) catalysts
title_sort green synthesis of 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol from natural d-sugars over au/al(2)o(3) and so(4)(2−)/al(2)o(3) catalysts
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8376872/
https://www.ncbi.nlm.nih.gov/pubmed/34413372
http://dx.doi.org/10.1038/s41598-021-96231-9
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