N-Thiodiglycoloyl derivatives of glucosamine as glycosyl donors

Autor:	Richard R. Schmidt, Julio C. Castro-Palomino
Rok vydání:	2000
Předmět:	Glycosylation Organic Chemistry Cleavage (embryo) Biochemistry Medicinal chemistry Catalysis chemistry.chemical_compound Acetic anhydride chemistry Glucosamine Drug Discovery Pyridine Glycosyl Dichloromethane
Zdroj:	Tetrahedron Letters. 41:629-632
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(99)02136-x
Popis:	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 Bu3SnH/AIBN and reacetylation with Ac2O/pyridine was employed, thus giving N-acetyl glucosamine containing compounds 7 and 10 in a convenient, high-yielding procedure.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3de78f6cdc0d513f3a4c2d61811521cc https://doi.org/10.1016/s0040-4039(99)02136-x Zobrazit plný text záznamu Full Text from ScienceDirect