Síntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucal
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFRPE |
Texto Completo: | http://www.tede2.ufrpe.br:8080/tede2/handle/tede2/7918 |
Resumo: | In this work, new glycoglycerolipids conjugates with triazole and pyrimidines were synthesized. Firstly, tri-O-acetyl-D-glucal 23 reacted with glycerol sulfite 58 in the presence of BF3Et2O to leads to diasteroisomers mixture of 2,3-unsaturated O-glucoside in 78% yield. Afterwards, reaction with sodium azide afforded the azido-glycero-glucoside 8-R,S-60 in 85% yield. Next, azido-glycoglycerolipid 61c was obtained in 56% yield after reaction with lauroyl chloride in the presence of DMAP/Et3N. The reaction of propargyl bromide with uracile, thymine or fluor-uracile, using K2CO3/DMF at room temperature leads to mono- and bis-alkylated pyrimidines 62-63 with yields of 20-35% and 74-86%, respectively. Thus, the propargylated pyrimidines were coupled with azido-glycoglycerolipid 61c via CuI-catalysis to furnish glycoglycerolipids 64a-c and 65a-c in yields ranging from 67 to 75% and from 43 to 48%, respectively. |
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OLIVEIRA, Ronaldo Nascimento deOLIVEIRA, Ronaldo Nascimento deMALVESTITI, IvaniFREITAS FILHO, João Rufino dehttp://lattes.cnpq.br/8039374118267678GUIMARÃES, Bruna Martins2019-04-03T13:06:22Z2018-03-07GUIMARÃES, Bruna Martins. Síntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucal. 2018. 107 f. Dissertação (Programa de Pós-Graduação em Química) - Universidade Federal Rural de Pernambuco, Recife.http://www.tede2.ufrpe.br:8080/tede2/handle/tede2/7918In this work, new glycoglycerolipids conjugates with triazole and pyrimidines were synthesized. Firstly, tri-O-acetyl-D-glucal 23 reacted with glycerol sulfite 58 in the presence of BF3Et2O to leads to diasteroisomers mixture of 2,3-unsaturated O-glucoside in 78% yield. Afterwards, reaction with sodium azide afforded the azido-glycero-glucoside 8-R,S-60 in 85% yield. Next, azido-glycoglycerolipid 61c was obtained in 56% yield after reaction with lauroyl chloride in the presence of DMAP/Et3N. The reaction of propargyl bromide with uracile, thymine or fluor-uracile, using K2CO3/DMF at room temperature leads to mono- and bis-alkylated pyrimidines 62-63 with yields of 20-35% and 74-86%, respectively. Thus, the propargylated pyrimidines were coupled with azido-glycoglycerolipid 61c via CuI-catalysis to furnish glycoglycerolipids 64a-c and 65a-c in yields ranging from 67 to 75% and from 43 to 48%, respectively.Neste trabalho, foram realizadas as sínteses de novos glicoglicerolipídios contendo os heterociclos 1,2,3-triazol e pirimidina. Primeiramente, o tri-O-acetil-D-glucal 23 reagiu com o sulfito de glicerol 58 na presença de BF3Et2O para fornecer uma mistura de distereoisômeros do glicosídeo 2,3-insaturado 59 com 78% de rendimento. Em seguida, reação com azida de sódio formou o azido-glicero-glicosídeo 8-R,S-60 com rendimento de 85%. Em seguida foi preparado o azido-glicoglicerolipídio 61c (56%) após reação com o cloreto de lauroíla na presença de DMAP/Et3N. As bases uracila, timina e flúor-uracila reagiram com brometo propargílico empregando DMF/K2CO3 a temperatura ambiente, formando as bases mono- e bis-alquiladas 62-63 com rendimentos de 20-35% e 74-86%, respectivamente. Na sequência, as bases propargílicas reagiram com o azido-glicoglicerolipídio 61c via reação catalisada por cobre formando os glicoglicerolipídios 64a-c e 65a-c com rendimentos de 67-75% e 43-48%, respectivamente.Submitted by Mario BC (mario@bc.ufrpe.br) on 2019-04-03T13:06:22Z No. of bitstreams: 1 Bruna Martins Guimaraes.pdf: 1776859 bytes, checksum: 0e60b28323a60941f16a679f5397fbe2 (MD5)Made available in DSpace on 2019-04-03T13:06:22Z (GMT). No. of bitstreams: 1 Bruna Martins Guimaraes.pdf: 1776859 bytes, checksum: 0e60b28323a60941f16a679f5397fbe2 (MD5) Previous issue date: 2018-03-07Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqCoordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESapplication/pdfporUniversidade Federal Rural de PernambucoPrograma de Pós-Graduação em QuímicaUFRPEBrasilDepartamento de QuímicaGlicoglicerolipídiosGlicerolTriazolPirimidinaCIENCIAS EXATAS E DA TERRA::QUIMICASíntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucalinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesis143564836222510089860060060060060038064160554570910301571700325303117195-25559114369857136592075167498588264571info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFRPEinstname:Universidade Federal Rural de Pernambuco (UFRPE)instacron:UFRPEORIGINALBruna Martins Guimaraes.pdfBruna Martins Guimaraes.pdfapplication/pdf1776859http://www.tede2.ufrpe.br:8080/tede2/bitstream/tede2/7918/2/Bruna+Martins+Guimaraes.pdf0e60b28323a60941f16a679f5397fbe2MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-82165http://www.tede2.ufrpe.br:8080/tede2/bitstream/tede2/7918/1/license.txtbd3efa91386c1718a7f26a329fdcb468MD51tede2/79182019-04-03 10:06:22.136oai:tede2: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Biblioteca Digital de Teses e Dissertaçõeshttp://www.tede2.ufrpe.br:8080/tede/PUBhttp://www.tede2.ufrpe.br:8080/oai/requestbdtd@ufrpe.br ||bdtd@ufrpe.bropendoar:2019-04-03T13:06:22Biblioteca Digital de Teses e Dissertações da UFRPE - Universidade Federal Rural de Pernambuco (UFRPE)false |
dc.title.por.fl_str_mv |
Síntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucal |
title |
Síntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucal |
spellingShingle |
Síntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucal GUIMARÃES, Bruna Martins Glicoglicerolipídios Glicerol Triazol Pirimidina CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucal |
title_full |
Síntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucal |
title_fullStr |
Síntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucal |
title_full_unstemmed |
Síntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucal |
title_sort |
Síntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucal |
author |
GUIMARÃES, Bruna Martins |
author_facet |
GUIMARÃES, Bruna Martins |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
OLIVEIRA, Ronaldo Nascimento de |
dc.contributor.referee1.fl_str_mv |
OLIVEIRA, Ronaldo Nascimento de |
dc.contributor.referee2.fl_str_mv |
MALVESTITI, Ivani |
dc.contributor.referee3.fl_str_mv |
FREITAS FILHO, João Rufino de |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/8039374118267678 |
dc.contributor.author.fl_str_mv |
GUIMARÃES, Bruna Martins |
contributor_str_mv |
OLIVEIRA, Ronaldo Nascimento de OLIVEIRA, Ronaldo Nascimento de MALVESTITI, Ivani FREITAS FILHO, João Rufino de |
dc.subject.por.fl_str_mv |
Glicoglicerolipídios Glicerol Triazol Pirimidina |
topic |
Glicoglicerolipídios Glicerol Triazol Pirimidina CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this work, new glycoglycerolipids conjugates with triazole and pyrimidines were synthesized. Firstly, tri-O-acetyl-D-glucal 23 reacted with glycerol sulfite 58 in the presence of BF3Et2O to leads to diasteroisomers mixture of 2,3-unsaturated O-glucoside in 78% yield. Afterwards, reaction with sodium azide afforded the azido-glycero-glucoside 8-R,S-60 in 85% yield. Next, azido-glycoglycerolipid 61c was obtained in 56% yield after reaction with lauroyl chloride in the presence of DMAP/Et3N. The reaction of propargyl bromide with uracile, thymine or fluor-uracile, using K2CO3/DMF at room temperature leads to mono- and bis-alkylated pyrimidines 62-63 with yields of 20-35% and 74-86%, respectively. Thus, the propargylated pyrimidines were coupled with azido-glycoglycerolipid 61c via CuI-catalysis to furnish glycoglycerolipids 64a-c and 65a-c in yields ranging from 67 to 75% and from 43 to 48%, respectively. |
publishDate |
2018 |
dc.date.issued.fl_str_mv |
2018-03-07 |
dc.date.accessioned.fl_str_mv |
2019-04-03T13:06:22Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
GUIMARÃES, Bruna Martins. Síntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucal. 2018. 107 f. Dissertação (Programa de Pós-Graduação em Química) - Universidade Federal Rural de Pernambuco, Recife. |
dc.identifier.uri.fl_str_mv |
http://www.tede2.ufrpe.br:8080/tede2/handle/tede2/7918 |
identifier_str_mv |
GUIMARÃES, Bruna Martins. Síntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucal. 2018. 107 f. Dissertação (Programa de Pós-Graduação em Química) - Universidade Federal Rural de Pernambuco, Recife. |
url |
http://www.tede2.ufrpe.br:8080/tede2/handle/tede2/7918 |
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por |
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por |
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openAccess |
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Universidade Federal Rural de Pernambuco |
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Programa de Pós-Graduação em Química |
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UFRPE |
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Departamento de Química |
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Universidade Federal Rural de Pernambuco |
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