Abstract:Bi(NO 3 ) 3 , a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high α-selectivity. Further, an expedient separation of α-and β-glycosides using silver nitrate-impregnated silica gel flash liquid chromatogr… Show more
“…Surprisingly, this catalyst was successful in facilitating the formation of exclusive β ‐products. Recently, Bhattacharrya and co‐workers also described the activation of both unprotected and unactivated glycosides by using 10 mol % of bismuth nitrate pentahydrate . The yields of the desired products were significantly increased when unprotected sugars were subjected to Fischer glycosylation by sulfamic acid .…”
The development of glycobiology relies on the sources of particular oligosaccharides in their purest forms. As the isolation of the oligosaccharide structures from natural sources is not a reliable option for providing samples with homogeneity, chemical means become pertinent. The growing demand for diverse oligosaccharide structures has prompted the advancement of chemical strategies to stitch sugar molecules with precise stereo‐ and regioselectivity through the formation of glycosidic bonds. This Review will focus on the key developments towards chemical O‐glycosylations in the current century. Synthesis of novel glycosyl donors and acceptors and their unique activation for successful glycosylation are discussed. This Review concludes with a summary of recent developments and comments on future prospects.
“…Surprisingly, this catalyst was successful in facilitating the formation of exclusive β ‐products. Recently, Bhattacharrya and co‐workers also described the activation of both unprotected and unactivated glycosides by using 10 mol % of bismuth nitrate pentahydrate . The yields of the desired products were significantly increased when unprotected sugars were subjected to Fischer glycosylation by sulfamic acid .…”
The development of glycobiology relies on the sources of particular oligosaccharides in their purest forms. As the isolation of the oligosaccharide structures from natural sources is not a reliable option for providing samples with homogeneity, chemical means become pertinent. The growing demand for diverse oligosaccharide structures has prompted the advancement of chemical strategies to stitch sugar molecules with precise stereo‐ and regioselectivity through the formation of glycosidic bonds. This Review will focus on the key developments towards chemical O‐glycosylations in the current century. Synthesis of novel glycosyl donors and acceptors and their unique activation for successful glycosylation are discussed. This Review concludes with a summary of recent developments and comments on future prospects.
“…1 H NMR spectroscopy was carried out with acetylated crude product to obtain the ratio of α- and β-anomers (Fig. 5 ) [ 22 ]. Fig.…”
Section: Use Of Different Catalysts and Additives For Fischer Glycosy...mentioning
confidence: 99%
“…The products were obtained in good to excellent yield and anomeric selectivity, with the α-anomer being predominant in all cases. The reaction method was compared with other previously reported methods for Fischer glycosylation based on temperature, reaction time, yield, and anomeric ratio (Table 15 ) [ 13 , 17 , 22 , 23 ].…”
Section: Use Of Different Catalysts and Additives For Fischer Glycosy...mentioning
confidence: 99%
“…The reaction method was compared with other previously reported methods for Fischer glycosylation based on temperature, reaction time, yield, and anomeric ratio (Table 15 ) [ 13 , 17 , 22 , 23 ].…”
Section: Use Of Different Catalysts and Additives For Fischer Glycosy...mentioning
Fischer glycosylation is typically the chemical reaction of a monosaccharide and an alcohol in presence of an acidic catalyst to afford glycosides in pyranosidic and furanosidic forms. This reaction is still applied today for the synthesis of specialized glycosides, and optimization and modification of the method have continued since its discovery by Emil Fischer in the 1890s. This review presents advancements in Fischer glycosylation described in literature of the past 15 years and its implementation in modern chemical methods.
“…Therefore, until date, the Fischer glycosylation is still an interesting method for the synthesis of glycosides [11]. Indeed, various variants have been implemented in the past decades including the use of microwave irradiation [12], various catalysts [13][14][15] and ionic liquids [16,17]. For these, however, challenges such as the thermodynamic handling of the chemical synthesis Article highlights • In the experiments in which 10-bromo-1-decanol was used as the bromoalcohol, yields were achieved exceeding more than 180% compared to other methods.…”
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 bromoalcohols were shown to be more compatible than shorter bromoalcohols under these reaction conditions.
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