Ultrasonic assisted Fischer glycosylation: generating diversity for glycochemistry |
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Authors: | Nasrin Shaikh Laura Russo Laura Cipolla Francesco Nicotra |
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Affiliation: | (1) Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand; |
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Abstract: | In this study ultrasound has been utilised for the Fischer glycosylation using free sugars and sulphuric acid immobilized on silica as catalyst. N-acetyl-d-glucosamine, N-acetyl-d-galactosamine, d-glucose, d-galactose, d-mannose, l-fucose, and lactose were glycosylated with propargyl alcohol or 2-azidoethanol affording the corresponding glycosides, with the production of the α-glycopyranoside as the dominant product. Remarkable acceleration of the glycosylation reactions (15 min–2 h compared to several hours) over reported procedures together with good yields were always observed. |
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