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Synthesis 2023; 55(07): 1087-1111
DOI: 10.1055/s-0042-1751394
DOI: 10.1055/s-0042-1751394
paper
Synthesis of the Three Most Expensive l-Hexose Thioglycosides from d-Glucose
The authors gratefully acknowledge financial support for this research from the Premium Postdoctoral Program of the Hungarian Academy of Science (PPD 461038, M.H.), the National Research and Development and Innovation Office of Hungary (FK 137924 M.H., K 132870, A.B. and NN 128368), and from the EU and co-financed by the European Regional Development Fund under the project GINOP-2.3.4-15-2020-00008.
Abstract
The biologically important l-hexoses, which are less widespread than d-hexoses, cannot be obtained from natural sources or can only be extracted very costly. Due to the complexity of their synthesis, their commercially available derivatives (which are sold mostly in free form) are also very expensive, which is further exacerbated by the current rapid rise in prices. In the present work, starting from the cheapest d-hexose, d-glucose, using inexpensive and readily available chemicals, a reaction pathway was developed in which the three most expensive l-hexoses (l-idose, l-altrose, and l-talose) were successfully prepared in orthogonally protected thioglycoside form, ready for glycosylation. The l-ido and l-talo derivatives were synthesized by C-5 epimerization of the corresponding 5,6-unsaturated thioglycosides. From the l-ido derivatives, the orthogonally protected thioglycosides of l-altrose were then prepared by C-4 epimerization. Different approaches to the preparation of the key intermediates, 5,6-unsaturated thioglycoside derivatives, were systematically investigated in the presence of various protecting groups (ether and ester) and using commercially available reagents.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751394.
- Supporting Information
Publication History
Received: 30 August 2022
Accepted after revision: 21 November 2022
Article published online:
21 December 2022
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