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Synthesis of a tri- and a hepta-saccharide which contain α-l-fucopyranosyl groups and are part of the complex type of carbohydrate moiety of glycoproteins

✍ Scribed by Hans Lönn

Publisher: Elsevier Science
Year: 1985
Tongue: English
Weight: 545 KB
Volume: 139
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(85)90011-4

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✦ Synopsis

Reaction of a thioglycoside with methyl trifluoromethanesulfonate (methyl triflate) in the presence of a hydroxyl compound is an efficient glycosylation method. Thus, methyl triflate-promoted condensation of ethyl 4,6-O-benzylidene-2 -deoxy-2-phthalimido-1-thio-3-0-(2,3,4-t~-O-benzyl-~-L-fucopyranosyl)-~-~-glucopyranoside with benzyl3,4,6-tri-O-benzyl-a-o-mannopyranoside and with benzyl 2,4-di-0-benzyl-3,6-di-0-(3,4,6-tri-O-benzyl-a-~-mannopyranosyl)-t-~-mannopyranoside gave a trisaccharide and a heptasaccharide derivative, respectively. The trisaccharide 1 and the heptasaccharide 2, which are parts of the complex type of glycoproteins, were obtained by removal of the protecting groups and N-acetylation.

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