A Direct Method for β-Selective Glycosylation with an N-Acetylglucosamine Donor Armed by a 4-O-TBDMS Protecting Group
Hidenori Tanaka1, Yu Hamaya2, Hiyoshizo Kotsuki3
1Oceanography Section, Science Research Center, Kochi University, Otsu, Nankoku-shi, Kochi 783-8502, Japan. htanaka@kochi-u.ac.jp.
Abstract:
A new direct method for β-selective glycosylation with an N-acetylglucosamine (GlcNAc) donor was developed. This substrate, which can be readily prepared from commercially available GlcNAc in two steps, contains a 4-O-tert-butyldimethylsilyl (TBDMS) protecting group as a key component. We found that this functionality could have a favorable effect on the reactivity of the GlcNAc donor. Glycosylation with the armed donor using primary alcohols in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf) in 1,2-dichloroethane smoothly gave the desired coupling products in good yields with complete β-selectivity, while sterically hindered acceptors were less efficient.
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