Selective pivaloylation of 2-acetamido-2-deoxy sugars.
Selective pivaloylation of 2-acetamido-2-deoxy-D-glucose, its methyl alpha- and beta-glycosides, and the methyl alpha-glycoside of N-acetyl-D-muramic acid under various conditions has been studied. The structures of the products were established by 1H-n.m.r. spectroscopy and acetylation. The orders of acylation, HO-6 greater than HO-3 greater than HO-1 greater than HO-4 for 2-acetamido-2-deoxy-D-glucose and HO-6 greater than HO-3 greater than HO-4 for its methyl glycosides, were established. Methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-alpha- and -beta-D-glucopyranosides and 2-acetamido-2-deoxy-1,3,4,6-tetra-O-pivaloyl-D-glucopyranose were hydrolysed by rabbit serum esterases.
Ljevaković
D
D
Department of Radioimmunology, Institute of Immunology, Zagreb, Yugoslavia.
Tomić
S
S
Tomasić
J
J
D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000378:metabolism*; D000215:Acylation; D000818:Animals; D005944:Glucosamine / Q000031:analogs & derivatives*; D008759:Methylglycosides / Q000378:metabolism*; D009112:Muramic Acids / Q000378:metabolism*; D010421:Pentanoic Acids / Q000378:metabolism*; D011817:Rabbits; D013400:Sugar Acids / Q000378:metabolism*; D014631:Valerates / Q000378:metabolism*
D008759:Methylglycosides; D009112:Muramic Acids; D010421:Pentanoic Acids; D013400:Sugar Acids; D014631:Valerates; C059103:methyl-2-acetamido-2-deoxy-3-O-(1-(methoxycarbonyl)ethyl)glucopyranoside; C059099:pivaloyl chloride; C014088:methyl-2-acetamido-2-deoxy-D-glucopyranoside; D005944:Glucosamine; D000117:Acetylglucosamine