University of Alabama Birmingham
A Synthesis and Characterization of D-Lyxo-Hexos-5-Ulose From D-Mannose.
Abstract
dc:description.abstractA 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.
Degree
thesis:*- Level thesis:degree_level
- Thesis
- Year
- 1980
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Harry-O'Kuru, Rogers E
Subjects
dc:subject × 4Identifiers
dc:identifier.*- Repository record dc:identifier
- https://digitalcommons.library.uab.edu/etd-collection/6975
- OAI identifier oai:identifier
- oai:digitalcommons.library.uab.edu:etd-collection-7967