2-Deoxyglycosides were synthesized in high α-selectivity by the direct addition of alcohols to D-glucal and D-galactal catalyzed by TMSI and PPh(3). The acid labile isopropylidene group is tolerated under this condition.
A possible catalytic role of pyridoxal-5'-phosphate in a general acid base catalyzed reaction of D-glucal with glycogen phosphorylases.
E J Helmreich et al.
Progress in clinical and biological research, 102 Pt C, 23-35 (1982-01-01)
The Journal of organic chemistry, 75(9), 3097-3100 (2010-04-13)
Novel one-pot three- and four-component transformations of D-glucal to furan-based hydroxy triazole glycoconjugates have been achieved by sequential addition of reagents in the presence of Cu(OTf)(2)-Cu powder as catalysts. In general the carbohydrate-derived products were formed with high diastereomeric purity.
The Journal of organic chemistry, 75(3), 955-958 (2010-01-14)
The conversion of cyclopropane-fused carbohydrates into oxepines is an attractive method for accessing diverse members of the septanoside family of carbohydrate mimetics. 2-Bromooxepines are obtained through silver(I)-promoted thermal ring expansion of a d-glucal-derived gem-dihalocyclopropanated sugar. In contrast, cyclopropane ring cleavage
D-Glucal, containing a highly reactive double bond, can replace glucose 1-phosphate as the glucosyl donor in phosphorylase-catalyzed glucosyl transfer to a suitable oligo- or polysaccharide acceptor: D-glucal + Pi + (glucose)Pi leads to n 2-deoxy-alpha-D-glucosyl(glucose)n in equilibrium 2-deoxy-alpha-D-glucose-1-P + (glucose)n.
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