Use of Acyclic Glycosyl Donors for Furanoside Synthesis

Autor:	Joseph C. McAuliffe, Ole Hindsgaul
Rok vydání:	1997
Předmět:	chemistry.chemical_compound chemistry Acetyl chloride Yield (chemistry) Organic Chemistry Organic chemistry Dimethylformamide Glycosyl Silver trifluoromethanesulfonate Methanol Carbohydrate Boron trifluoride
Zdroj:	The Journal of Organic Chemistry. 62:1234-1239
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo9618583
Popis:	Treatment of the peracetylated ethyl dithioacetals of d-glucose, d-galactose, and d-mannose with acetyl chloride and boron trifluoride diethyl etherate at reflux yields the known acyclic 1-chloro-1-(ethylthio) derivatives. These compounds are shown to effectively glycosylate a variety of carbohydrate acceptors using silver trifluoromethanesulfonate as the promotor, affording stereospecifically the corresponding acyclic O,S-acetals in good to excellent yield. Furthermore, following deacetylation, treatment of these O,S-acetals with a mixture of mercuric salts in either methanol or dimethylformamide gives rise to disaccharides terminating in d-furanosyl residues.
Databáze:	OpenAIRE
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