Synthesis and intramolecular transesterifications of pivaloylated methyl alpha-D-galactopyranosides.
Selective pivaloylations of methyl alpha-D-galactopyranoside have been studied under various reaction conditions. Partially pivaloylated products were submitted to additional acetylations. The structures were established by 1H and 13C NMR spectroscopies. Both, 2,6- and 3,6-dipivalates underwent intramolecular cyclization in neutral conditions (phosphate buffered saline, pH 7.2) to give a stable 2,3-orthoacid with a parallel 6-->4 migration of the pivaloyl group.
Petrović
Vesna
V
Department of Chemistry, Faculty of Science, University of Zagreb, Strossmayerov trg 14, Croatia.
Tomić
Srdanka
S
Matanović
Maja
M
D000818:Animals; D002236:Carbohydrate Conformation; D004951:Esterification; D005690:Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D006168:Guinea Pigs; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011817:Rabbits
C469243:methyl-galactopyranoside; D005690:Galactose