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Highly beta-selective glucosylations of glycosyl acceptors having alpha primary hydroxy group with a 6-nitro-2-benzothia-zolyl alpha-glucoside donor 3alpha proceeded smoothly in the presence of a catalytic amount of trifluoromethanesulfonic acid (TfOH) in CH 2Cl2 at -78 C to afford the corresponding glycosides in high yields. With the use of 3alpha, beta-saccharides could be obtained more dominantly than other alpha-glucosyl donors such as thioform- and trichloroacet-imidates or fluoride in the glucosylation under the same conditions. Similarly, highly beta-selective mannosylations of glycosyl acceptors with a 6-nitro-2-benzothiazolyl alpha-mannoside donor 18alpha were carried out smoothly in the presence of a catalytic amount of tetrakis(pentafluorophenyl)boric acid H[B(C6F5) 4] to afford the corresponding disaccharides in good to high yields; 18alpha apparently behaved as a potent donor here for the construction of beta-mannoside linkage. Interestingly, in situ anomerization from 18beta to 18alpha was observed when beta-mannosyl donor 18beta was treated with a catalytic amount of H[B(C6F5)4] in CH 2Cl2.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics