{"id":{"repo_id":"uab","oai_identifier":"oai:digitalcommons.library.uab.edu:etd-collection-7967"},"canonical_url":"https://search.dev.ndltd.org/etd/uab/oai:digitalcommons.library.uab.edu:etd-collection-7967","repository":{"repo_id":"uab","name":"University of Alabama Birmingham","base_url":"https://digitalcommons.library.uab.edu/do/oai/"},"display":{"title":"A Synthesis and Characterization of D-Lyxo-Hexos-5-Ulose From D-Mannose.","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.","abstract_html":"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.","abstract_has_math":false,"creators":["Harry-O'Kuru, Rogers E"],"institution":null,"degree_name":null,"degree_level":"Thesis","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1980,"date_issued":"1980-01-01T08:00:00Z","date_published":"1980-01-01T08:00:00Z","updated_at":"2026-07-24T05:06:03Z","subjects":["D-mannose","Triphenylmethyl","Acetic anhydride","Hydroxyl group"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://digitalcommons.library.uab.edu/etd-collection/6975","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Harry-O'Kuru, Rogers E"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"thesis:degree_level","label":"Degree Level","values":["Thesis"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["D-mannose","Triphenylmethyl","Acetic anhydride","Hydroxyl group"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://digitalcommons.library.uab.edu/etd-collection/6975"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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."]},{"key":"dc:title","label":"Title","values":["A Synthesis and Characterization of D-Lyxo-Hexos-5-Ulose From D-Mannose."]}]}],"canonical_facts":{"dc:creator":["Harry-O'Kuru, Rogers E"],"dc:description.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."],"dc:identifier":["https://digitalcommons.library.uab.edu/etd-collection/6975"],"dc:subject":["D-mannose","Triphenylmethyl","Acetic anhydride","Hydroxyl group"],"dc:title":["A Synthesis and Characterization of D-Lyxo-Hexos-5-Ulose From D-Mannose."],"thesis:degree_level":["Thesis"]},"updated_at":"2026-07-24T05:06:03Z"}