1-Butanol, reactions with carbohydrates

By means of an ETHOS MR oven, Nuchter et al. [33] accomplished scaling-up of a microwave-assisted Fischer glycosylation to the kilogram scale with improved economic efficiency. In batch reactions, carbohydrates (o-glucose, o-mannose, d-galactose, butyl o-galactose, starch) were converted on the 50-g scale (95-100% yield, from 95 5 to 100%) with 3-30-fold molar excesses of an alcohol (methanol, ethanol, butanol, octanol) in the presence of a catalytic amount of acetyl chloride under pressure (microwave flow reactor, 120-140 °C, 12-16 bar, 5-12 min) or without applying pressure (120-140 °C or reflux temperature, 20-60 min). Furano-sides are not stable under these reaction conditions. 

The incorporation of cyclic carbohydrates into Gemini surfactants was developed by Castro et al. (Rg. 7.27) [56]. These sugar geminis have been synthesized from AGs which can be easily prepared via a Rsher-type glycosylation reaction of free glucose by w-butanol. Convenient protection of the sugar moiety, followed by selective deprotection of the primary alcohol, permits the formation of gemini 12 by a double esterification with propanedicarboxylic acid. 

Most studies of enzymatic sugar ester synthesis have focused on the esterification of monosaccharides, since the problems with poor substrate miscibility increase significantly with increasing size of the carbohydrate. However, by careful choice of reaction conditions it has been shown possible to acylate several di- and trisaccharides efficiently. Solvent mixtures of 2-methyl-2-butanol and dimethylsulfoxide have thus been used in... 

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