Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5266246 | Tetrahedron Letters | 2013 | 4 Pages |
Abstract
Dipyrranes bearing peracetylated mono- or disaccharidic C-1-deoxyalditol moieties were prepared from d-galactose, d-glucose, d-mannose, and lactose. A partially hydrolyzed polysaccharide (agarose) was also used as starting material for the synthesis of a disaccharide-containing C-glycoside dipyrrane. These compounds were synthesized as follows: the sugar starting materials were first submitted to a mercaptolysis-acetylation one-pot procedure (EtSH/HCl-Ac2O/pyridine). The resulting peracetylated diethyl dithioacetals were converted into dipyrranes through carbonyl deprotection (H5IO6, THF-Et2O) followed by TFA-catalyzed pyrrole condensation with yields up to 62%. Overall yields from sugar starting materials were up to 49%.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Stephanie M.S. Ló, Juliana C. Cunico, Diogo R.B. Ducatti, Alexandre Orsato, M. Eugênia R. Duarte, Sandra M.W. Barreira, Miguel D. Noseda, Alan G. Gonçalves,