Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH(4)

An improved method to efficiently synthesize 2-OH thioaryl glycosides starting from corresponding per-protected glycals was developed, where 1,2-anhydro sugars were prepared by the oxidation of glycals with oxone, followed by reaction of crude crystalline 1,2-anhydro sugars with NaBH(4) and aryl dis...

Descripción completa

Detalles Bibliográficos
Autores principales: Guo, Yang-Fan, Luo, Tao, Feng, Guang-Jing, Liu, Chun-Yang, Dong, Hai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9506437/
https://www.ncbi.nlm.nih.gov/pubmed/36144712
http://dx.doi.org/10.3390/molecules27185980
_version_ 1784796722757632000
author Guo, Yang-Fan
Luo, Tao
Feng, Guang-Jing
Liu, Chun-Yang
Dong, Hai
author_facet Guo, Yang-Fan
Luo, Tao
Feng, Guang-Jing
Liu, Chun-Yang
Dong, Hai
author_sort Guo, Yang-Fan
collection PubMed
description An improved method to efficiently synthesize 2-OH thioaryl glycosides starting from corresponding per-protected glycals was developed, where 1,2-anhydro sugars were prepared by the oxidation of glycals with oxone, followed by reaction of crude crystalline 1,2-anhydro sugars with NaBH(4) and aryl disulfides. This method has been further used in a one-pot reaction to synthesize glycosyl donors having both “armed” and “NGP (neighboring group participation)” effects.
format Online
Article
Text
id pubmed-9506437
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-95064372022-09-24 Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH(4) Guo, Yang-Fan Luo, Tao Feng, Guang-Jing Liu, Chun-Yang Dong, Hai Molecules Article An improved method to efficiently synthesize 2-OH thioaryl glycosides starting from corresponding per-protected glycals was developed, where 1,2-anhydro sugars were prepared by the oxidation of glycals with oxone, followed by reaction of crude crystalline 1,2-anhydro sugars with NaBH(4) and aryl disulfides. This method has been further used in a one-pot reaction to synthesize glycosyl donors having both “armed” and “NGP (neighboring group participation)” effects. MDPI 2022-09-14 /pmc/articles/PMC9506437/ /pubmed/36144712 http://dx.doi.org/10.3390/molecules27185980 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Guo, Yang-Fan
Luo, Tao
Feng, Guang-Jing
Liu, Chun-Yang
Dong, Hai
Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH(4)
title Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH(4)
title_full Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH(4)
title_fullStr Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH(4)
title_full_unstemmed Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH(4)
title_short Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH(4)
title_sort efficient synthesis of 2-oh thioglycosides from glycals based on the reduction of aryl disulfides by nabh(4)
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9506437/
https://www.ncbi.nlm.nih.gov/pubmed/36144712
http://dx.doi.org/10.3390/molecules27185980
work_keys_str_mv AT guoyangfan efficientsynthesisof2ohthioglycosidesfromglycalsbasedonthereductionofaryldisulfidesbynabh4
AT luotao efficientsynthesisof2ohthioglycosidesfromglycalsbasedonthereductionofaryldisulfidesbynabh4
AT fengguangjing efficientsynthesisof2ohthioglycosidesfromglycalsbasedonthereductionofaryldisulfidesbynabh4
AT liuchunyang efficientsynthesisof2ohthioglycosidesfromglycalsbasedonthereductionofaryldisulfidesbynabh4
AT donghai efficientsynthesisof2ohthioglycosidesfromglycalsbasedonthereductionofaryldisulfidesbynabh4

Ejemplares similares