Spectinomycin modification. II. Spectinomycin C-3'-modification via diazoketone intermediates.
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.
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D055598:Chemical Phenomena; D002621:Chemistry; D003978:Diazomethane / Q000031:analogs & derivatives*; D006860:Hydrogen Bonding; D000198:Spectinomycin; D013329:Structure-Activity Relationship
C015795:diazomethyl ketones; D003978:Diazomethane; D000198:Spectinomycin