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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-...

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Autores principales: Hore, Ratul, Halder, Tapas, Pradhan, Anirban, Mukherjee, Souvik, Maity, Joykrishna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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.
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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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