Low-concentration 1,2-trans beta-selective glycosylation strategy and its applications in oligosaccharide synthesis.
This study develops an operationally easy, efficient, and general 1,2-trans beta-selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent beta-selectivities in glycosylation reactions. This method is widely applicable to a range of glycosyl substrates irrespective of their structures and hydroxyl-protecting functions. This low-concentration 1,2-trans beta-selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2-trans beta-glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant beta-(1-->6)-glucan trisaccharide, beta-linked Gb(3) and isoGb(3) derivatives.
Chao
Chin-Sheng
CS
Department of Applied Chemistry, National Chiao Tung University, Taiwan, ROC, 1001, Ta Hsueh Road, Hsinchu, Taiwan.
Li
Chen-Wei
CW
Chen
Min-Chun
MC
Chang
Shih-Sheng
SS
Mong
Kwok-Kong Tony
KK