Superbase-catalyzed stereo- and regioselective glycosylation with 2‑nitroglycals : facile access to 2‑amino-2-deoxy‑O‑glycosides
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 und...
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2020
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| Online Access: | https://hdl.handle.net/10356/144910 |
| _version_ | 1826125693327507456 |
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| author | Pal, Kumar Bhaskar Guo, Aoxin Das, Mrinmoy Báti, Gábor Liu, Xue-Wei |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Pal, Kumar Bhaskar Guo, Aoxin Das, Mrinmoy Báti, Gábor Liu, Xue-Wei |
| author_sort | Pal, Kumar Bhaskar |
| collection | NTU |
| description | 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. |
| first_indexed | 2024-10-01T06:40:52Z |
| format | Journal Article |
| id | ntu-10356/144910 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:40:52Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1449102023-02-28T19:48:54Z Superbase-catalyzed stereo- and regioselective glycosylation with 2‑nitroglycals : facile access to 2‑amino-2-deoxy‑O‑glycosides Pal, Kumar Bhaskar Guo, Aoxin Das, Mrinmoy Báti, Gábor Liu, Xue-Wei School of Physical and Mathematical Sciences Science::Chemistry 2-Nitroglycals Superbase 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. Accepted version 2020-12-03T02:45:46Z 2020-12-03T02:45:46Z 2020 Journal Article 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 2155-5435 https://hdl.handle.net/10356/144910 10.1021/acscatal.0c00753 12 10 6707 6715 en NRF2016NRF-NSFC002-005 ACS Catalysis 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 application/pdf |
| spellingShingle | Science::Chemistry 2-Nitroglycals Superbase Pal, Kumar Bhaskar Guo, Aoxin Das, Mrinmoy Báti, Gábor Liu, Xue-Wei Superbase-catalyzed stereo- and regioselective glycosylation with 2‑nitroglycals : facile access to 2‑amino-2-deoxy‑O‑glycosides |
| title | Superbase-catalyzed stereo- and regioselective glycosylation with 2‑nitroglycals : facile access to 2‑amino-2-deoxy‑O‑glycosides |
| title_full | Superbase-catalyzed stereo- and regioselective glycosylation with 2‑nitroglycals : facile access to 2‑amino-2-deoxy‑O‑glycosides |
| title_fullStr | Superbase-catalyzed stereo- and regioselective glycosylation with 2‑nitroglycals : facile access to 2‑amino-2-deoxy‑O‑glycosides |
| title_full_unstemmed | Superbase-catalyzed stereo- and regioselective glycosylation with 2‑nitroglycals : facile access to 2‑amino-2-deoxy‑O‑glycosides |
| title_short | Superbase-catalyzed stereo- and regioselective glycosylation with 2‑nitroglycals : facile access to 2‑amino-2-deoxy‑O‑glycosides |
| title_sort | superbase catalyzed stereo and regioselective glycosylation with 2 nitroglycals facile access to 2 amino 2 deoxy o glycosides |
| topic | Science::Chemistry 2-Nitroglycals Superbase |
| url | https://hdl.handle.net/10356/144910 |
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