77895-19-3

Upstream product

• 2403-88-5 4-hydroxy-2,2,6,6-tetramethylpiperidine 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 54423-54-0 2,3,4,6-Tetra-O-benzyl 1-O-p-nitrobenzoyl D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of alpha- and beta-glycosides containing spin labels, as probes for studies of carbohydrate-protein interaction.

Nitroxide spin-labeled alpha-D-glycopyranosides were synthesized in good yield and in a highly stereoselective manner by reaction of per-O-benzyl-alpha-D-glycopyranosyl bromides with 2,2,6,6-tetramethyl-4-piperidinol under the bromide ion-catalyzed conditions devised by Lemieux et al. After hydrogenolysis, the deblocked intermediates were oxidized to give the desired, spin-labeled alpha-D-glycopyranosides. Nitroxide spin-labeled beta-D-glycopyranosides, as well as a beta-maltoside, were synthesized by standard methods. The synthesis is also described of 2-amino-2-deoxy-D-glucose and -D-galactose derivatives having a spin label at C-2, and of the spin-labeled compound 1-[4-(beta-D-galactopyranosyloxy)phenyl]-3-(2,2,6,6-tetramethylpiperidin-1-oxyl -4-yl)-2-thiourea.