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Spectinomycin modification 2. spectinomycin carbon 3' modification via diazoketone intermediates






Journal of Antibiotics (Tokyo) 38(2): 197-207

Spectinomycin modification 2. spectinomycin carbon 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 H bonding groups in this region of the molecule for good activity, further refining the structure activity relationships in the spectinomycin series.


Accession: 006459325



Related references

Thomas, R.C.; Fritzen, E.L., 1985: 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 o...

Thomas, R.C.; Fritzen, E.L., 1985: Spectinomycin modification 3. spectinomycin analogs with carbon 3' branched chain sugars. A variety of C-3'-branched chain analogs of spectinomycin was synthesized via the intermediacy of spectinomycin derived diazoketones. In vitro antibacterial assay of these compounds underscored the importance of H bonding functional groups in...

Thomas, R.C.; Fritzen, E.L., 1988: Spectinomycin modification. V. The synthesis and biological activity of spectinomycin analogs with ring-expanded sugars. Tiffeneau-Demjanov rearrangement of 3'-(R)-N,N'-dibenzyloxycarbonyl-3'-aminomethyl-dihydrospectinom ycin results in ring expansion affording the homologous analog with a seven-membered sugar ring. In stark contrast, attempted rearra...

Thomas, R.C.; Fritzen, E.L., 1985: Spectinomycin modification. III. Spectinomycin analogs with C-3'-branched chain sugars. A variety of C-3'-branched chain analogs of spectinomycin has been synthesized via the intermediacy of spectinomycin derived diazoketones. In vitro antibacterial assay of these compounds has underscored the importance of hydrogen bonding func...

Thomas, R.C.; Fritzen, E.L., 1988: Spectinomycin modification. IV. The synthesis of 3'-aminomethyldihydrospectinomycins via spectinomycin 3'-cyanohydrins. The C-3'-carbonyl group of N-protected spectinomycin is converted into the corresponding aminomethylalcohols via the intermediacy of cyanohydrins. Methodology for the selective synthesis of either epimer with retention of protection in the am...

Rosenbrook W.Jr; Carney R.E., 1975: Spectinomycin modification part 1 7 epi 9 deoxy 4 r di hydro spectinomycin. Journal of Antibiotics (Tokyo) 28(12): 953-959

Rosenbrook, W.J. ; Carney, R.E.; Egan, R.S.; Stanaszek, R.S.; Cirovic, M.; Nishinaga, T.; Mochida, K.; Mori, Y., 1978: Spectinomycin modification part 4 7 deoxy 4r di hydro spectinomycin. 7-Deoxy-4(R)-dihydrospectinomycin was prepared and its structure firmly established by PMR and high resolution mass spectrometry. This spectinomycin analog is devoid of antibiotic activity.

Thomas, R.C., 1982: Spectinomycin modification 1. catalytic n demethylation of spectinomycin. Treatment of an aqueous solution of spectinomycin dihydrochloride with O2 and Pt black results in N-demethylation, affording the partially and fully N-demethylated spectinomycins in good yield. The 1:1 mixture of mono-N-demethylspectinomycins has...

Thomas, R.C., 1982: Spectinomycin modification. I. Catalytic N-demethylation of spectinomycin. Treatment of an aqueous solution of spectinomycin dihydrochloride with O2 and Pt black results in N-demethylation, affording the partially and fully N-demethylated spectinomycins in good yield. The 1:1 mixture of mono-N-demethylspectinomycins has...

Rosenbrook W.Jr; Carney R.E.; Egan R.S.; Stanaszek R.S.; Cirovic M.; Nishinaga T.; Mochida K.; Mori Y., 1975: Spectinomycin modification part 2 7 epi spectinomycin. Journal of Antibiotics (Tokyo) 28(12): 960-964