The synthesis of 2-acetamido-2-deoxy-4-O- -L-fucopyranosyl- -D-glucose |
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| Authors: | M A Shaban R W Jeanloz |
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| Affiliation: | 1. National Glycoengineering Research Center and Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, Qingdao 266237, China;2. NMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate-based Medicine, Shandong University, Qingdao 266237, China;1. Bionanomanufacturing Center, IPT – Institute for Technological Research, Sao Paulo, SP, Brazil;2. Department of Bioinformatics, UFMG – Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil;3. Department of Statistics, University of Oxford, Oxford, UK;4. Universidade Federal de São Paulo (UNIFESP), São Paulo, SP, Brazil |
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| Abstract: | Condensation of 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide with the 2,3-carbonate of 2-amino-2-deoxy-5,6-O-isopropylidene-D-glucose diethyl acetal, in the presence of mercuric cyanide or silver carbonate, gave the 2,3-carbonate of 2-amino-2-deoxy-5,6-O-isopropylidene-4-O-(tri-O-acetyl-α-L-fucopyranosyl)-D-glucose diethyl acetal in 32 and 13% yield, respectively. Hydrolysis of the acetyl and carbonate protective groups by alkali, and of the acetal and isopropylidene groups by acid, followed by introduction of an N-acetyl group, gave the title disaccharide, which was characterized by a hexa-O-acetyl derivative. This disaccharide is useful as a reference compound in the study of the carbohydrate fragments obtained by enzymic hydrolysis, or partial hydrolysis with acid, or glycoproteins and glycolipids, and as a starting material for their synthesis. |
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