Stereoselective synthesis of [13C]methyl 2-[15N]amino-2-deoxy-β-d-glucopyranoside derivatives Original Research Article

Efficient syntheses of three [13C]methyl 2-[15N]amino-2-deoxy-β-d-glucopyranoside derivatives are described. Amination of the d-glucal with (saltmen)Mn(15N) proceeded with 11:1 stereoselectivity favoring the gluco configuration; subsequent methylation of the [15N]lactol using [13C]iodomethane and silver(I) oxide afforded the doubly labeled β glucoside in high yield. This compound served as the common precursor for three [13C]methyl 2-[15N]aminoglucosides: (2-[15N]trifluoroacetyl-), (2-[15N]acetyl-), and (2-[15N]azido-). Selected heteronuclear coupling constants are reported.