Synthesis of potassium (2R)-2-O-alpha-d-glucopyranosyl-(1-->6)-alpha-d-glucopyranosyl-2,3-dihydroxypropanoate a natural compatible solute.
Ethyl 6-O-acetyl-2,3,4-tribenzyl-1-thio-d-glucopyranoside, as a mixture of anomers, was employed for the stereoselective synthesis of the potassium salt of (2R)-2-O-alpha-d-glucopyranosyl-(1-->6)-alpha-d-glucopyranosyl-2,3-dihydroxypropanoic acid (alpha-d-glucosyl-(1-->6)-alpha-d-glucosyl-(1-->2)-d-glyceric acid, GGG), a recently isolated compatible solute. The alpha-anomer was by far the major product of both glycosylation reactions using NIS/TfOH as activator.
Lourenço
Eva C
EC
Instituto de Tecnologia Química e Biológica, Universidade Nova de Lisboa, Oeiras, Portugal.
Maycock
Christopher D
CD
Rita Ventura
M
M
D005988:Glyceric Acids / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry*
D005988:Glyceric Acids; D013865:Thioglycosides; C042971:glyceric acid