BROMOHYDROXYLATION OF GLYCALS—AN INVESTIGATION INTO THE REACTION OF SOME 4-N-ACYLATED DERIVATIVES OF METHYL 5-ACETAMIDO-7,8,9-TRI-O-ACETYL-2,6-ANHYDRO-3,4,5-TRIDEOXY-D-GLYCERO-D-GALACTO-NON-2-ENONATE AND ITS 4-EPIMER

Autor:	Gaik B. Kok, Tho van Phan, Mark von Itzstein
Rok vydání:	2001
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Reaction temperature chemistry Glycal Stereochemistry Organic Chemistry Substituent Stereoselectivity Glycosyl Epimer Solvent composition Biochemistry
Zdroj:	Journal of Carbohydrate Chemistry. 20:359-374
ISSN:	1532-2327 0732-8303
Popis:	Bromohydroxylation of some 4-N-acylated derivatives of the glycals of N-acetylneuraminic acid, methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate (4) and methyl 5-aceta-mido-7,8,9-tri-O-acetyl-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-talo-non-2-enonate (the 4-epimer of 4), with N-bromosuccinimide (NBS) and water in the presence of a co-solvent has provided a range of new glycosyl donors. The stereoselectivity of the halohydroxylation reaction was found to be governed by solvent composition, reaction temperature and the stereoelectronic nature of the substituent at C-4.
Databáze:	OpenAIRE
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