N-Thiodiglycoloyl derivatives of glucosamine as glycosyl donors

N-Thiodiglycoloyl (TDG) protection of O-acetylated glucosamine could be readily carried out with thiodiglycolic anhydride and then treatment with acetic anhydride in pyridine. Ensuing reaction with hydrazinium acetate and then base-catalyzed activation with trichlorocetonitrile afforded N-TDG protec...

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Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 5; pp. 629 - 632
Main Authors Castro-Palomino, Julio C, Schmidt, Richard R
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.01.2000
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
GLYCOPEPTIDES
TRICHLOROACETIMIDATE
OLIGOSACCHARIDES
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Summary:N-Thiodiglycoloyl (TDG) protection of O-acetylated glucosamine could be readily carried out with thiodiglycolic anhydride and then treatment with acetic anhydride in pyridine. Ensuing reaction with hydrazinium acetate and then base-catalyzed activation with trichlorocetonitrile afforded N-TDG protected glucosamine donor 3. Glycosylation of acceptors 8 and 5 in dichloromethane with TMSOTf as the catalyst gave β-glycosides 6 and 9 in high yields. For TDG cleavage MeONa/MeOH treatment followed by radical desulfurization with Bu 3SnH/AIBN and reacetylation with Ac 2O/pyridine was employed, thus giving N-acetyl glucosamine containing compounds 7 and 10 in a convenient, high-yielding procedure.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)02136-X