2021
DOI: 10.1007/s41981-021-00202-0
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Continuous synthesis of bromoalkyl glycosides by Fischer glycosylation in a microreactor

Abstract: In this study, bromoalkyl glycosides were successfully synthesized in microreactor scale by Fischer glycosylation. Yields between 24 and 40% after purification were achieved using various acidic catalysts and conditions. In some experiments, yields 180% higher than with previously known methods could be achieved. This study showed also that reversed-phase flash chromatography is more successful than normal-phase flash chromatography for the purification of bromoalkyl glycosides. Furthermore, longer bromoalcoho… Show more

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Cited by 4 publications
(5 citation statements)
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“…Microreactors are also a safer alternative for MW Fischer glycosylation, where a headspace is created through flammable alcohols, which represents an explosion hazard. Figure 13 shows the synthesis of bromoalkyl glucosides from d -glucose and bromoalcohols promoted by an acidic catalyst [ 59 ].
Fig.
…”
Section: Fischer Glycosylation In Reactorsmentioning
confidence: 99%
See 2 more Smart Citations
“…Microreactors are also a safer alternative for MW Fischer glycosylation, where a headspace is created through flammable alcohols, which represents an explosion hazard. Figure 13 shows the synthesis of bromoalkyl glucosides from d -glucose and bromoalcohols promoted by an acidic catalyst [ 59 ].
Fig.
…”
Section: Fischer Glycosylation In Reactorsmentioning
confidence: 99%
“…The crude product was purified first with column chromatography, and after combining the fractions containing bromoalkyl glucosides, organic solvents were removed under reduced pressure to allow further refinement of the product with lyophilization. Anomeric ratios were detected with 1 H and 13 C NMR spectroscopy [ 59 ].
Fig.
…”
Section: Fischer Glycosylation In Reactorsmentioning
confidence: 99%
See 1 more Smart Citation
“…However, TMSOTf assisted glycosylation yielded up to 40% bromoalkyl glycoside (121) in the scale-up process. 73 Vicenistatin is a novel 20-membered polyketide macrocyclic lactam antibiotic having antitumor activity against human colon carcinoma Co-3. 74,75 When polyene lactam (123) was glycosylated with 2-deoxy-glycosyl fluoride (122) in the presence of TMSOTf as the promoter, followed by the cleavage of the carbamate under basic pH, vicenistatin (124) and its a-anomer were produced in 10% and 18% yields, respectively (Scheme 31).…”
Section: Silane Assisted Glycosylation For the Synthesis Of Apis And ...mentioning
confidence: 99%
“…However, TMSOTf assisted glycosylation yielded up to 40% bromoalkyl glycoside ( 121 ) in the scale-up process. 73…”
Section: Silane Assisted Glycosylation For the Synthesis Of Apis And ...mentioning
confidence: 99%