The application of the intermediate 2-methyl-glyco-[2,1-d]-2-oxazolines for glycoside synthesis.
The synthesis of 2-acylamino-2-deoxysugars 1,2-trans-glycosides is described via the oxazolinium salt generated from an O,N-acetylated 1,2-cis-glycosyl halide of 2-amino-2-deoxysugar under the conditions of halide-anion catalysis. This salt was then interacted with alcohol to form the corresponding 1,2-trans-glycoside. A method for removing the generated hydrogen chloride is described. The conditions of this synthesis allow glycosides with acid-labile functional groups to be obtained. Suppression of the anomerisation of 1,2-trans-glycosides was achieved by the introduction of N,N'-dicyclohexyl urea into the reaction medium.
Pertel
S S
SS
Department of Organic Chemistry, National Taurida University, Crimea, Ukraine. orgchem@ccssu.crimea.ua
Chirva
V Y
VY
Kadun
A L
AL
Kakayan
E S
ES
D000438:Alcohols / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D012492:Salts / Q000737:chemistry
D000438:Alcohols; D006027:Glycosides; D010080:Oxazoles; D012492:Salts