Regio- and Stereoselective Synthesis of Thioglycosides from 4,5-Diphenyl- and 3,4,5-Triphenylimidazole-2-thione

Autor:	El Sayed H. El Ashry, Nagat Rezki, Nagwa Rashed, S. M. Abdel-Maggeed, El Sayed Ramadan, Laila F. Awad
Rok vydání:	2009
Předmět:	chemistry.chemical_classification Anomer Glycosylation Chemistry Stereochemistry Organic Chemistry Oligosaccharide Biochemistry Combinatorial chemistry Inorganic Chemistry chemistry.chemical_compound Microwave irradiation Moiety Glycosyl Stereoselectivity Triethylamine
Zdroj:	Phosphorus, Sulfur, and Silicon and the Related Elements. 184:1759-1767
ISSN:	1563-5325 1042-6507
Popis:	Six new thioglycosides incorporating the 4,5-diphenyl- and 3,4,5-triphenylimidazole moiety have been successfully synthesized under both conventional and microwave conditions by reaction of the corresponding thiones with aceto-bromosugars in presence of triethylamine as base. Attempted preparation of the bis(glycosyl) derivatives from 4,5-diphenylimidazole-2-thione in the presence of different bases was unsuccessful. Evaluation of the glycosylthioimidazoles as disarmed donors has been investigated using different promoters; NBS/TMSOTf has been found to be an effective promoter for the activation of the anomeric center towards glycosylation reaction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9db64ca8f066618605a446ece2932341 https://doi.org/10.1080/10426500802339873 Zobrazit plný text záznamu