Regioselective Dehydration of Sugar Thioacetals under Mild Conditions

[Image: see text] Sugars are abundant in waste biomass, making them sustainable chiral building blocks for organic synthesis. The demand for chiral saturated heterocyclic rings for pharmaceutical applications is increasing as they provide well-defined three-dimensional frameworks that show increased...

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Autores principales: Szpara, Rachel, Goyder, Alexander, Porter, Michael J., Hailes, Helen C., Sheppard, Tom D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8041386/
https://www.ncbi.nlm.nih.gov/pubmed/33729808
http://dx.doi.org/10.1021/acs.orglett.1c00424
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author Szpara, Rachel
Goyder, Alexander
Porter, Michael J.
Hailes, Helen C.
Sheppard, Tom D.
author_facet Szpara, Rachel
Goyder, Alexander
Porter, Michael J.
Hailes, Helen C.
Sheppard, Tom D.
author_sort Szpara, Rachel
collection PubMed
description [Image: see text] Sugars are abundant in waste biomass, making them sustainable chiral building blocks for organic synthesis. The demand for chiral saturated heterocyclic rings for pharmaceutical applications is increasing as they provide well-defined three-dimensional frameworks that show increased metabolic resistance. A range of sugar thioacetals can be dehydrated selectively at C-2 under mild basic conditions, and the resulting ketene thioacetals can be applied to the production of useful chiral building blocks via further selective dehydration reactions.
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spelling pubmed-80413862021-04-13 Regioselective Dehydration of Sugar Thioacetals under Mild Conditions Szpara, Rachel Goyder, Alexander Porter, Michael J. Hailes, Helen C. Sheppard, Tom D. Org Lett [Image: see text] Sugars are abundant in waste biomass, making them sustainable chiral building blocks for organic synthesis. The demand for chiral saturated heterocyclic rings for pharmaceutical applications is increasing as they provide well-defined three-dimensional frameworks that show increased metabolic resistance. A range of sugar thioacetals can be dehydrated selectively at C-2 under mild basic conditions, and the resulting ketene thioacetals can be applied to the production of useful chiral building blocks via further selective dehydration reactions. American Chemical Society 2021-03-17 2021-04-02 /pmc/articles/PMC8041386/ /pubmed/33729808 http://dx.doi.org/10.1021/acs.orglett.1c00424 Text en © 2021 The Authors. Published by American Chemical Society Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Szpara, Rachel
Goyder, Alexander
Porter, Michael J.
Hailes, Helen C.
Sheppard, Tom D.
Regioselective Dehydration of Sugar Thioacetals under Mild Conditions
title Regioselective Dehydration of Sugar Thioacetals under Mild Conditions
title_full Regioselective Dehydration of Sugar Thioacetals under Mild Conditions
title_fullStr Regioselective Dehydration of Sugar Thioacetals under Mild Conditions
title_full_unstemmed Regioselective Dehydration of Sugar Thioacetals under Mild Conditions
title_short Regioselective Dehydration of Sugar Thioacetals under Mild Conditions
title_sort regioselective dehydration of sugar thioacetals under mild conditions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8041386/
https://www.ncbi.nlm.nih.gov/pubmed/33729808
http://dx.doi.org/10.1021/acs.orglett.1c00424
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