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Title: Programmable selective acylation of saccharides mediated by carbene and boronic acid
Authors: Lv, Wen-Xin
Chen, Hang
Zhang, Xinglong
Ho, Chang Chin
Liu, Yingguo
Wu, Shuquan
Wang, Haiqi
Jin, Zhichao
Chi, Robbin Yonggui
Keywords: Science::Chemistry
Issue Date: 2022
Source: Lv, W., Chen, H., Zhang, X., Ho, C. C., Liu, Y., Wu, S., Wang, H., Jin, Z. & Chi, R. Y. (2022). Programmable selective acylation of saccharides mediated by carbene and boronic acid. Chem, 8(5), 1518-1534.
Project: NRF-NRFI2016-06
MOE2019- T2-2-117
Journal: Chem
Abstract: 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.
ISSN: 2451-9308
DOI: 10.1016/j.chempr.2022.04.019
Schools: School of Physical and Mathematical Sciences 
Rights: © 2022 Elsevier Inc. All rights reserved. This paper was published in Chem and is made available with permission of Elsevier Inc.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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