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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