title: Spectinomycin modification. II. Spectinomycin C-3'-modification via diazoketone intermediates.
abstract: The C-3'-carbonyl group of N-protected spectinomycin is efficiently converted into a diazo group via base treatment of the corresponding tosylhydrazone. The diazo group imparts a new synthetically useful reactivity pattern on the sugar ring of the molecule. The synthesis of C-3'-deoxo-, monohalo- and dihalospectinomycins via the intermediacy of these diazo compounds is described. The reduced bioactivity of these analogs as compared to the parent and the C-3'-dihydro and aminospectinomycins established the need for hydrogen bonding groups in this region of the molecule for good activity, further refining the structure activity relationships in the spectinomycin series.
authors.forename: R C
authors.initials: RC
authors.lastname: Thomas
authors.forename: E L
authors.initials: EL
authors.lastname: Fritzen
mesh_terms: D055598:Chemical Phenomena; D002621:Chemistry; D003978:Diazomethane / Q000031:analogs & derivatives*; D006860:Hydrogen Bonding; D000198:Spectinomycin; D013329:Structure-Activity Relationship
chemical_list: C015795:diazomethyl ketones; D003978:Diazomethane; D000198:Spectinomycin