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Title: A minimalist approach to stereoselective glycosylation with unprotected donors
Authors: Hoang, Kim Le Mai
He, Jing-xi
Báti, Gábor
Chan-Park, Mary B.
Liu, Xue-Wei
Keywords: Glycosylation
Issue Date: 2017
Source: Hoang, K. L. M., He, J.-x., Báti, G., Chan-Park, M. B., & Liu, X.-W. (2017). A minimalist approach to stereoselective glycosylation with unprotected donors. Nature Communications, 8(1), 1146-.
Series/Report no.: Nature Communications
Abstract: Mechanistic study of carbohydrate interactions in biological systems calls for the chemical synthesis of these complex structures. Owing to the specific stereo-configuration at each anomeric linkage and diversity in branching, significant breakthroughs in recent years have focused on either stereoselective glycosylation methods or facile assembly of glycan chains. Here, we introduce the unification approach that offers both stereoselective glycosidic bond formation and removal of protection/deprotection steps required for further elongation. Using dialkylboryl triflate as an in situ masking reagent, a wide array of glycosyl donors carrying one to three unprotected hydroxyl groups reacts with various glycosyl acceptors to furnish the desired products with good control over regioselectivity and stereoselectivity. This approach demonstrates the feasibility of straightforward access to important structural scaffolds for complex glycoconjugate synthesis.
DOI: 10.1038/s41467-017-01073-7
Rights: © 2017 The Author(s) (Nature Publishing Group). 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 license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license 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 license, visit licenses/by/4.0/.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SCBE Journal Articles
SPMS Journal Articles

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