ChemInform Abstract: Syntheses and Structures of Anomeric Quaternary Ammonium β‐Glucosides and Comments on the Anomeric C—N Bonds Lengths.

Abstract

Carbohydrates U 0500Syntheses and Structures of Anomeric Quaternary Ammonium β-Glucosides and Comments on the Anomeric C-N Bonds Lengths. -Two general methods for the synthesis of tertiary glycosylamines and their quaternization are presented. One approach involves the reductive N,N-dimethylation of a protected anomeric glycosylamine, quaternization with alkyl halides, and deacetylation without loss of the ammonium group. The other is based on the direct reaction of glucose or 6-O-trityl glucose with a secondary amine, followed by protection and quaternization with a triflate. -(IDDON, L.; BRAGG, R. A.; HARDING, J. R.; PIDATHALA, C.; BACSA, J.; KIRBY, A. J.; STACHULSKI*, A. V.; Tetrahedron 65 (2009) 32, 6396-6402; Robert Robinson Lab., Dep. Chem., Univ. Liverpool, Liverpool L69 7ZD, UK; Eng.) -Klein 47-178