Microwave-induced synthesis of 2,3-unsaturated O-glycosides under solvent-free conditions

Recent Developments in the Ferrier Rearrangement

“…Reactions between glucal 5 and a variety of phenols assisted by microwave irradiation techniques have also been described 35. However, this procedure failed when cyclohexanol was used as nucleophile 36…”

The use of tri-O-acetyl-d-glucal and -d-galactal in the synthesis of ω-aminoalkyl 2-deoxy- and 2,3-dideoxy-d-hexopyranosides

“…This is a Ferrier reaction, which occurs through rearrangement. [22][23][24][25][26][27][28] The appropriate products of Ferrier's rearrangement, 4,6-di-O-acetyl-2,3-dideoxyhexenopyranosides 6a-e, were achieved in satisfactory yield (Scheme 2). The NMR data indicated the formation of a-anomers exclusively (Table 1, entries [7][8][9][10][11].…”

O-Glicosídeos 2,3-Insaturados: Aplicações, Rearranjo De Ferrier E Reações

“…93,94 As modificações mais expressivas são a mudança de catalisadores e o uso de novas fontes de energia, como o uso da irradiação de micro--ondas por exemplo. 95 Em 2010, Menezes et al 96 utilizaram como catalisador o TeBr 4 para promover a síntese de O-glicosídeos 2,3-insaturados (Esquema 13). Neste trabalho os autores observaram uma alta seletividade anomérica no uso desse catalisador, uma diminuição drástica no tempo reacional (2-30 minutos) e rendimentos de bons a excelentes (70-94%).…”