Y. Nishida, H. Hori, H. Ohrui
Apr 23, 1988
Citations
0
Influential Citations
6
Citations
Journal
Agricultural and biological chemistry
Abstract
Four stereoisomers of methyl 4,6-di-O-d-glucopyranosyl-β-d-glucopyranosides, in which the H-6proiS proton at the (1→6)-linkage moiety was selectively replaced by a deuterium (2H), were synthesized through the photobromination of 1,6-anhydro-per-O-acetyl-β-d-maltopyranose and β-d-glucose, with subsequent deuteride reduction of the brominated products (C-6exo bromides) by tri-n-butyltin deuteride. The chirally deuterated sugars enabled us to differentiate the H-6proR and H-6proS signals at the (1→6)-linkage moiety and, thereby, to clarify the conformational distributions about the C5-C6 bonds.