Journal
CHEM
Volume 8, Issue 5, Pages 1518-1534Publisher
CELL PRESS
DOI: 10.1016/j.chempr.2022.04.019
Keywords
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Categories
Funding
- Singapore National Research Foundation under its NRF Investigatorship [NRF-NRFI2016-06]
- Competitive Research Program [NRF-CRP22-2019-0002]
- Singapore Ministry of Education [RG7/20, RG5/19, MOE-2019T2-2-117, MOE2018-T3-1-003]
- Nanyang Technological University
- National Natural Science Foundation of China [21772029, 21801051, 21807019, 21961006, 22071036, 22061007, 22101266]
- Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules of the Guizhou Province Department of Education [Qianjiaohe KY (2020) 004]
- 10 Talent Plan (Shicengci) of Guizhou Province [[2016]5649]
- Science and Technology Department of Guizhou Province [[2018]2802, [2019]1020]
- Guizhou University Program of Introducing Talents of Discipline to Universities of China (111 Program) [D20023]
- Guizhou University
- Agency for Science, Technology and Research(A*STAR) Institute of High Performance Computing
- A*STAR Deputy Chief Executive Research Office for a Career Development Fund [C210812008]
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Chemical synthesis or modification of saccharides is difficult due to the challenge of site-selective reactions on their similar hydroxyl groups. The lack of efficient tools hinders the understanding of saccharide-related biological processes and the development of saccharide-based pharmaceuticals. In this study, a programmable multilayered selectivity-amplification strategy using boronic acids and N-heterocyclic carbene (NHC) catalysts is presented for site-specific acylation of monoglycosides.
Chemical synthesis or modification of saccharides remains a major challenge largely because site-selective reactions on their many similar hydroxyl groups are difficult. The lack of efficient chemical synthetic tools has therefore become a main obstacle to understanding saccharide-related biological processes and developing saccharide-based pharmaceuticals. Here, we disclose a programmable multilayered selectivity-amplification strategy enabled by boronic acids and N-heterocyclic carbene (NHC) catalysts for site specific acylation of unprotected monoglycosides. The boronic acids provide transient shielding on certain hydroxyl groups (while simultaneously promoting reactions of other hydroxyl units) via dynamic covalent bonds to offer the first sets of selectivity controls. The NHC catalysts provide further layers of control by mediating selective acylation of the unshielded hydroxyl moieties. Multiple activating and deactivating forces can be easily modulated to yield programmable selectivity patterns. Structurally diverse monosaccharides and their analogs can be precisely reacted with different acylating reagents, leading to quick construction of sophisticated saccharide-derived products.
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