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2. Improved catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate: application to various 1-hydroxy sugars

Author

Toshiaki Sunazuka, Tatsuya Shirahata, Satoko Teruya, Nozomu Hirata, Jun-ichi Matsuo, Satoshi Ōmura, Nanao Akimoto, Taku Kurimoto, and Eisuke Kaji

Subjects
Glycosylation, Magnetic Resonance Spectroscopy, animal structures, Stereochemistry, Carbohydrates, macromolecular substances, Biochemistry, Catalysis, Analytical Chemistry, chemistry.chemical_compound, Organic chemistry, Glycosyl, Lewis acids and bases, Glycosyl donor, Molecular Structure, Organic Chemistry, Glycosyl acceptor, Chemical glycosylation, Stereoisomerism, General Medicine, carbohydrates (lipids), Models, Chemical, chemistry, lipids (amino acids, peptides, and proteins), Stereoselectivity, Carbamates
Abstract

Efficient catalytic and stereoselective glycosylation was achieved by activating a glycosyl N -trichloroacetylcarbamate with a catalytic amount of Lewis acid in the presence of a glycosyl acceptor and 5 Ǻ molecular sieves. Catalytic one-pot dehydrative glycosylation of a 1-hydroxy carbohydrate was achieved stereoselectively by reaction with trichloroacetyl isocyanate, followed by activation with a catalytic amount of activators.

Published
2010
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