Systematic synthesis and characterization of a series of different bromoalkylglycosides by Fischer glycosylation

Continuous synthesis of bromoalkyl glycosides by Fischer glycosylation in a microreactor

“…Therefore, it can be expected that even higher yields in the overall process can be achieved when using more reaction solution, as the losses in the overall process do not change. This would also be a possible explanation for the fact that the yields in the experiments with 6-bromo-1-hexanol were lower than in Williams et al [18]. Also, one important difference between experiments 12 and 13 was that experiment number 13 used three times the reactants and catalyst than experiment number 12.…”

“…Furthermore, it is not certain what influence the solvent dependent dilution of the reaction solution has on the yield. Williams et al [18] did not use a solvent in their experiments. Omitting the solvent could possibly further increase the yield of product.…”

“…Yields of between 24 and 40% could be achieved in this project. Williams et al [18] reported a yield of 39% in experiments with 6-bromo-1-hexanol, a yield of 27% in experiments with 8-bromo-1-octanol, as well as a yield of 18% in experiments using 10-bromo-1-decanol. Thus, in this project, the yields could be increased by approximately 150% in the experiments with 8-bromo-1-octanol and by more than 180% in experiments with 10-bromo-1-decanol.…”

“…of glycosides by Fischer glycosylation must be overcome. A promising approach for this is the production of bromoalkyl glycosides in a continuously operated microreactor [18]. Microreactors are alreasdy used today for various organic syntheses [19].…”

Like Visiting an Old Friend: Fischer Glycosylation in the Twenty-First Century: Modern Methods and Techniques

“…bromoalcohol relative to the monosaccharide was the lowest amount necessary to perform the glycosylation reaction. Results of the experiments are presented in Table 20 [ 34 ].…”