Document Type
Thesis
Date of Award
1980
Abstract
A convenient synthesis of 5-keto-mannose (D-lyxo-hexos-5-ulose, 20) from D-mannose is described. Methyl 2,3-0-isopropylidene-a-D-manno furanoside was converted to its crystalline 6-0-triphenylmethyl ether which in turn was oxidized at the C-5 hydroxyl group with either methylsulfoxide/acetic anhydride or ruthenium tetraoxide/sodium periodate to methyl 2,3-0-isopropylidene-6-0-triphenylmethyl-α-D-lyxo-hexos-5-ulose. Mild acidic hydrolysis conditions cleaved the triphenyl- methyl group from 17 giving crystalline methyl 2,3-0-isopropylidene-α-D-lyxo-hexos-5-ulose, which was water soluble enough to be easily separated from triphenylcarbinol. The protecting groups on 19 were hydrolytically removed in the presence of H+ form resin to give the target compound 20. 5-Keto-mannose was characterized directly by 13C and high field (400 MHz) 1H n.m.r. and indirectly by GC/MS as its fully trimethylsilylated dioxime.
Recommended Citation
Harry-O'Kuru, Rogers E., "A Synthesis and Characterization of D-Lyxo-Hexos-5-Ulose From D-Mannose." (1980). All ETDs from UAB. 6975.
https://digitalcommons.library.uab.edu/etd-collection/6975
Comments
MS - Master of Science/Master of Surgery; ProQuest publication number 31751895