Iron(III) chloride catalyzed glycosylation of peracylated sugars with allyl/alkynyl alcohols

Abstract

Neste trabalho, o emprego de cloreto férrico como um eficiente catalisador em reações de glicosilação de açúcares na presença de álcoois alílicos e propargílicos é descrito. Os glicosídios correspondentes foram obtidos com rendimentos de moderados a bons. Este novo procedimento apresenta maior seletividade quando comparado a métodos clássicos encontrados na literatura. As principais características desse método simples incluem condições de reação não perigosas, quantidade de catalisador baixa, bom rendimento e seletividade anomérico elevada.In this work, the use of ferric chloride as an efficient catalyst in glycosylation reactions of sugars in the presence of allyl and alkynyl alcohols is described. The corresponding glycosides were obtained with moderate to good yields. This new procedure presented greater selectivity when compared to classic methods found in the literature. Principal features of this simple method include non-hazardous reaction conditions, low-catalyst loading, good yields and high anomeric selectivity.

Iron Catalysis in Organic Synthesis

“…Glycosidic allylation and propargylation of various peracetylated mono- and disugars has been achieved by Paixão et al using iron(III) chloride as catalyst (Scheme ) . A pronounced selectivity for the anomeric position could be observed providing the glycosidic products in moderate to good yields under very mild conditions.…”

Síntese, assinalamento completo e estudo do perfil farmacocinético, bioativo e de toxicidade do 2-propin-1-il 2,3,4,6-tetra-O-acetil-β-D-glicopiranose

“…Assim, a reação de glicosilação entre o 1,2,3,4,6-penta-O-acetil-β-D-glicopiranose (1) e o 2-propin-1-ol (2) catalisada por BF3•(OCH3)2 levou ao glicosídeo 3 em 4,0 h e em um bom rendimento (87%) (Figura 2). Dentre as metodologias descritas na literatura para reação de glicosilação [35,36,37], este método foi escolhido devido a sua eficiência e tolerância a diferentes grupos funcionais.…”

Green Synthesis Characterization and Thermotropic Behaviour of O-Linked Glycopyranosides of Phenolic Esters

“…According to literature guidelines, glycosylation reactions have been executed by employing various solvents such as dichloromethane, tetrahydrofuran, toluene [6], dioxane [7,8] and dimethylformamide [9,10]. e variety of catalyst ranges from the organic catalyst such as N-iodosuccinimide, boron trifluoride etherate, 4-dimethylaminopyridine, pentamethyldiethylenetriamine, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide to the metal catalyst including tin tetrachloride and indium [11][12][13][14][15][16][17][18][19][20]. However, their toxicity, prohibitive prices and increased waste disposal costs add up to serious drawbacks for the large-scale applications.…”