Please use this identifier to cite or link to this item:
https://hdl.handle.net/10356/144910
Title: | Superbase-catalyzed stereo- and regioselective glycosylation with 2‑nitroglycals : facile access to 2‑amino-2-deoxy‑O‑glycosides | Authors: | Pal, Kumar Bhaskar Guo, Aoxin Das, Mrinmoy Báti, Gábor Liu, Xue-Wei |
Keywords: | Science::Chemistry | Issue Date: | 2020 | Source: | Pal, K. B., Guo, A., Das, M., Báti, G., & Liu, X.-W. (2020). Superbase-catalyzed stereo- and regioselective glycosylation with 2‑nitroglycals : facile access to 2‑amino-2-deoxy‑O‑glycosides. ACS Catalysis, 10(12), 6707-6715. doi:10.1021/acscatal.0c00753 | Project: | NRF2016NRF-NSFC002-005 | Journal: | ACS Catalysis | Abstract: | An efficient superbase-catalyzed stereo- and regio-selective glycosylation of 2-nitroglycals with high functional group compatibility is reported. The ion pair generated from alcohol and a catalytic amount of P4-t-Bu was vital for the successful implementation of this stereoselective glycosylation under mild conditions, producing moderate to good yields. Under reported reaction conditions, 2-nitrogalactals produce α-stereoisomers exclusively, while 2-nitroglucal yielded more β-products. The notable difference between the outcomes was investigated by the density functional theory (DFT) study. In addition, we have synthesized the key intermediate of a mucin-type core-6 glycoconjugate, thus illustrating the synthetic potency of this method. | URI: | https://hdl.handle.net/10356/144910 | ISSN: | 2155-5435 | DOI: | 10.1021/acscatal.0c00753 | Rights: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.0c00753 | Fulltext Permission: | open | Fulltext Availability: | With Fulltext |
Appears in Collections: | SPMS Journal Articles |
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Superbase-Catalyzed Stereo- and Regioselective Glycosylation with 2‑Nitroglycals Facile Access to 2‑Amino-2-deoxy‑O‑glycosides.pdf | 1.7 MB | Adobe PDF | View/Open |
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