Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a key precursor of the C33-C37 fragment of calyculins

Detalhes bibliográficos
Autor(a) principal: Cironi,Pablo
Data de Publicação: 2001
Outros Autores: Varela,Oscar
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532001000500010
Resumo: 3,4-Di-O-benzyl-1-O-methyl-L-galactitol (3) has been synthesized in a seven step sequence starting from 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose (4). The synthesis involves the methyllation of HO-6 of 4, followed by methanolysis to the mixture of the corresponding methyl 6-O-methyl-alpha-D-galactopyranoside (6, major product) and the beta-furanoside analog (8). Compound 6 was converted into the 3,4-O-isopropylidene derivative 9, and the free HO-group was protected as the methoxyethoxymethyl (MEM) ether. Chemoselective removal of the acetonide by hydrolysis, followed by benzylation gave the methyl 3,4-di-O-benzyl-2-O-methoxyethoxymethyl-6- O-methyl-alpha-D-galactopyranoside (12). Simultaneous acid hydrolysis of the methyl glycoside and MEM group of 12 led to 13, which was then reduced with sodium borohydride to the target molecule 3.
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spelling Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a key precursor of the C33-C37 fragment of calyculinscalyculinssecondary metabolitesmarine spongegalactose diacetonideL-galactitol derivative3,4-Di-O-benzyl-1-O-methyl-L-galactitol (3) has been synthesized in a seven step sequence starting from 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose (4). The synthesis involves the methyllation of HO-6 of 4, followed by methanolysis to the mixture of the corresponding methyl 6-O-methyl-alpha-D-galactopyranoside (6, major product) and the beta-furanoside analog (8). Compound 6 was converted into the 3,4-O-isopropylidene derivative 9, and the free HO-group was protected as the methoxyethoxymethyl (MEM) ether. Chemoselective removal of the acetonide by hydrolysis, followed by benzylation gave the methyl 3,4-di-O-benzyl-2-O-methoxyethoxymethyl-6- O-methyl-alpha-D-galactopyranoside (12). Simultaneous acid hydrolysis of the methyl glycoside and MEM group of 12 led to 13, which was then reduced with sodium borohydride to the target molecule 3.Sociedade Brasileira de Química2001-10-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532001000500010Journal of the Brazilian Chemical Society v.12 n.5 2001reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532001000500010info:eu-repo/semantics/openAccessCironi,PabloVarela,Oscareng2001-10-31T00:00:00Zoai:scielo:S0103-50532001000500010Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2001-10-31T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a key precursor of the C33-C37 fragment of calyculins
title Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a key precursor of the C33-C37 fragment of calyculins
spellingShingle Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a key precursor of the C33-C37 fragment of calyculins
Cironi,Pablo
calyculins
secondary metabolites
marine sponge
galactose diacetonide
L-galactitol derivative
title_short Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a key precursor of the C33-C37 fragment of calyculins
title_full Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a key precursor of the C33-C37 fragment of calyculins
title_fullStr Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a key precursor of the C33-C37 fragment of calyculins
title_full_unstemmed Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a key precursor of the C33-C37 fragment of calyculins
title_sort Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a key precursor of the C33-C37 fragment of calyculins
author Cironi,Pablo
author_facet Cironi,Pablo
Varela,Oscar
author_role author
author2 Varela,Oscar
author2_role author
dc.contributor.author.fl_str_mv Cironi,Pablo
Varela,Oscar
dc.subject.por.fl_str_mv calyculins
secondary metabolites
marine sponge
galactose diacetonide
L-galactitol derivative
topic calyculins
secondary metabolites
marine sponge
galactose diacetonide
L-galactitol derivative
description 3,4-Di-O-benzyl-1-O-methyl-L-galactitol (3) has been synthesized in a seven step sequence starting from 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose (4). The synthesis involves the methyllation of HO-6 of 4, followed by methanolysis to the mixture of the corresponding methyl 6-O-methyl-alpha-D-galactopyranoside (6, major product) and the beta-furanoside analog (8). Compound 6 was converted into the 3,4-O-isopropylidene derivative 9, and the free HO-group was protected as the methoxyethoxymethyl (MEM) ether. Chemoselective removal of the acetonide by hydrolysis, followed by benzylation gave the methyl 3,4-di-O-benzyl-2-O-methoxyethoxymethyl-6- O-methyl-alpha-D-galactopyranoside (12). Simultaneous acid hydrolysis of the methyl glycoside and MEM group of 12 led to 13, which was then reduced with sodium borohydride to the target molecule 3.
publishDate 2001
dc.date.none.fl_str_mv 2001-10-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532001000500010
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532001000500010
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532001000500010
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.12 n.5 2001
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
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instname_str Sociedade Brasileira de Química (SBQ)
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institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
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