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Easy Access to Sauropunols A–D: Synthesis and Spectroscopy Correlation of Their Natural Methyl and Ethyl Glycosides
[Image: see text] 3,6-Anhydro-2-deoxy-hexofuranoside, the natural product core, is present in natural sauropunols (A–D) and in their natural methyl and ethyl glycosides, now, namely, sauropunol H and sauropunol F. The easily synthesized d-glucose-derived 3,6-anhydro-1,2-O-isopropylidene-5-O-benzoyl-...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10601080/ https://www.ncbi.nlm.nih.gov/pubmed/37901566 http://dx.doi.org/10.1021/acsomega.3c05742 |
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author | Hore, Ratul Halder, Tapas Pradhan, Anirban Mukherjee, Souvik Maity, Joykrishna |
author_facet | Hore, Ratul Halder, Tapas Pradhan, Anirban Mukherjee, Souvik Maity, Joykrishna |
author_sort | Hore, Ratul |
collection | PubMed |
description | [Image: see text] 3,6-Anhydro-2-deoxy-hexofuranoside, the natural product core, is present in natural sauropunols (A–D) and in their natural methyl and ethyl glycosides, now, namely, sauropunol H and sauropunol F. The easily synthesized d-glucose-derived 3,6-anhydro-1,2-O-isopropylidene-5-O-benzoyl-α-d-glucofuranose was elaborated to final targets employing the TsOH·H(2)O-catalyzed glycosylation reaction with seven different alcohols, subsequent radical deoxygenation, and appropriate deprotection reactions involving mild conditions with excellent functional group tolerance. A short total synthesis of sauropunols (A–D), sauropunol H, and the first total synthesis of sauropunol F are reported herein. The correlation of spectroscopy data of sauropunol H and sauropunol F has been derived through these syntheses. |
format | Online Article Text |
id | pubmed-10601080 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-106010802023-10-27 Easy Access to Sauropunols A–D: Synthesis and Spectroscopy Correlation of Their Natural Methyl and Ethyl Glycosides Hore, Ratul Halder, Tapas Pradhan, Anirban Mukherjee, Souvik Maity, Joykrishna ACS Omega [Image: see text] 3,6-Anhydro-2-deoxy-hexofuranoside, the natural product core, is present in natural sauropunols (A–D) and in their natural methyl and ethyl glycosides, now, namely, sauropunol H and sauropunol F. The easily synthesized d-glucose-derived 3,6-anhydro-1,2-O-isopropylidene-5-O-benzoyl-α-d-glucofuranose was elaborated to final targets employing the TsOH·H(2)O-catalyzed glycosylation reaction with seven different alcohols, subsequent radical deoxygenation, and appropriate deprotection reactions involving mild conditions with excellent functional group tolerance. A short total synthesis of sauropunols (A–D), sauropunol H, and the first total synthesis of sauropunol F are reported herein. The correlation of spectroscopy data of sauropunol H and sauropunol F has been derived through these syntheses. American Chemical Society 2023-10-16 /pmc/articles/PMC10601080/ /pubmed/37901566 http://dx.doi.org/10.1021/acsomega.3c05742 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Hore, Ratul Halder, Tapas Pradhan, Anirban Mukherjee, Souvik Maity, Joykrishna Easy Access to Sauropunols A–D: Synthesis and Spectroscopy Correlation of Their Natural Methyl and Ethyl Glycosides |
title | Easy Access to
Sauropunols A–D: Synthesis and
Spectroscopy Correlation of Their Natural Methyl and Ethyl Glycosides |
title_full | Easy Access to
Sauropunols A–D: Synthesis and
Spectroscopy Correlation of Their Natural Methyl and Ethyl Glycosides |
title_fullStr | Easy Access to
Sauropunols A–D: Synthesis and
Spectroscopy Correlation of Their Natural Methyl and Ethyl Glycosides |
title_full_unstemmed | Easy Access to
Sauropunols A–D: Synthesis and
Spectroscopy Correlation of Their Natural Methyl and Ethyl Glycosides |
title_short | Easy Access to
Sauropunols A–D: Synthesis and
Spectroscopy Correlation of Their Natural Methyl and Ethyl Glycosides |
title_sort | easy access to
sauropunols a–d: synthesis and
spectroscopy correlation of their natural methyl and ethyl glycosides |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10601080/ https://www.ncbi.nlm.nih.gov/pubmed/37901566 http://dx.doi.org/10.1021/acsomega.3c05742 |
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