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...

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Bibliographic Details
Published inCarbohydrate research Vol. 182; no. 2; p. 197
Main Authors Ljevaković, D, Tomić, S, Tomasić, J
Format Journal Article
LanguageEnglish
Published Netherlands 01.11.1988
Subjects
Acetylglucosamine - analogs & derivatives
Acetylglucosamine - metabolism
Acylation
Animals
Glucosamine - analogs & derivatives
Methylglycosides - metabolism
Muramic Acids - metabolism
Pentanoic Acids - metabolism
Rabbits
Sugar Acids - metabolism
Valerates - metabolism
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Summary: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.
ISSN:0008-6215
DOI:10.1016/0008-6215(88)84003-5