A concise synthesis of carbasugars isolated from Streptomyces lincolnensis

Detalhes bibliográficos
Autor(a) principal: Holmstedt, Suvi
Data de Publicação: 2020
Outros Autores: Candeias, Nuno R.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10773/36646
Resumo: (–)-Quinic acid was used as a starting material in the hemisynthesis of two epimeric carbasugars isolated from Streptomyces lincolnensis. Previous 10–12 steps syntheses for the carbasugars have been herein shortened to 4–6 steps by using quinic acid as a chiron, based on a regioselective reduction step, with stereoinversion of a tertiary center. Both C-5 epimers of (1R, 2R, 3R)-5-(hydroxymethyl)cyclohexane-1,2,3-triol were obtained in up to 76% overall yield.
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spelling A concise synthesis of carbasugars isolated from Streptomyces lincolnensisCarbasugarChironCyclitolHemisynthesisQuinic acid(–)-Quinic acid was used as a starting material in the hemisynthesis of two epimeric carbasugars isolated from Streptomyces lincolnensis. Previous 10–12 steps syntheses for the carbasugars have been herein shortened to 4–6 steps by using quinic acid as a chiron, based on a regioselective reduction step, with stereoinversion of a tertiary center. Both C-5 epimers of (1R, 2R, 3R)-5-(hydroxymethyl)cyclohexane-1,2,3-triol were obtained in up to 76% overall yield.Elsevier2023-03-24T16:33:16Z2020-12-18T00:00:00Z2020-12-18info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10773/36646eng0040-402010.1016/j.tet.2020.131346Holmstedt, SuviCandeias, Nuno R.info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-05-06T04:43:44Zoai:ria.ua.pt:10773/36646Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-06T04:43:44Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv A concise synthesis of carbasugars isolated from Streptomyces lincolnensis
title A concise synthesis of carbasugars isolated from Streptomyces lincolnensis
spellingShingle A concise synthesis of carbasugars isolated from Streptomyces lincolnensis
Holmstedt, Suvi
Carbasugar
Chiron
Cyclitol
Hemisynthesis
Quinic acid
title_short A concise synthesis of carbasugars isolated from Streptomyces lincolnensis
title_full A concise synthesis of carbasugars isolated from Streptomyces lincolnensis
title_fullStr A concise synthesis of carbasugars isolated from Streptomyces lincolnensis
title_full_unstemmed A concise synthesis of carbasugars isolated from Streptomyces lincolnensis
title_sort A concise synthesis of carbasugars isolated from Streptomyces lincolnensis
author Holmstedt, Suvi
author_facet Holmstedt, Suvi
Candeias, Nuno R.
author_role author
author2 Candeias, Nuno R.
author2_role author
dc.contributor.author.fl_str_mv Holmstedt, Suvi
Candeias, Nuno R.
dc.subject.por.fl_str_mv Carbasugar
Chiron
Cyclitol
Hemisynthesis
Quinic acid
topic Carbasugar
Chiron
Cyclitol
Hemisynthesis
Quinic acid
description (–)-Quinic acid was used as a starting material in the hemisynthesis of two epimeric carbasugars isolated from Streptomyces lincolnensis. Previous 10–12 steps syntheses for the carbasugars have been herein shortened to 4–6 steps by using quinic acid as a chiron, based on a regioselective reduction step, with stereoinversion of a tertiary center. Both C-5 epimers of (1R, 2R, 3R)-5-(hydroxymethyl)cyclohexane-1,2,3-triol were obtained in up to 76% overall yield.
publishDate 2020
dc.date.none.fl_str_mv 2020-12-18T00:00:00Z
2020-12-18
2023-03-24T16:33:16Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10773/36646
url http://hdl.handle.net/10773/36646
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0040-4020
10.1016/j.tet.2020.131346
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv mluisa.alvim@gmail.com
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