B. Coxon, R. Reynolds
1980
Citations
0
Influential Citations
11
Citations
Journal
Carbohydrate Research
Abstract
Abstract Derivatives of 6-amino-6-deoxy- D -galactose-6-15N have been synthesized by reaction of the 6-deoxy-6-iodo (1) or 6-O-p-tolylsulfonyl derivative of 1,2:3,4-di-O-isopropylidene-α- D -galactopyranose with potassium phthalimide-15N. The reaction of 1 also yielded an elimination product, 6-deoxy-1,2:3,4-di-O-isopropylidene-β- L -arabino-hex-5-enopyranose. The structures of the 6-amino-6-deoxy- D -galactose derivatives and their precursors were characterized by proton- and 13C-n.m.r. spectroscopy, with confirmation of the 13C assignments by selective proton decoupling. Selective broadening of the C-1, C-4, C-5, and C-6 resonances of 6-amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α- D -galactopyranose by low concentrations of cupric ion was observed, and studied by computerized measurements of the 13C linewidths. The application of this broadening to 13C-spectral assignments of amino sugar derivatives is indicated.