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Spectinomycin modification part 4 7 deoxy 4r di hydro spectinomycin






Journal of Antibiotics (Tokyo) 31(5): 451-455

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.


Accession: 006459327



Related references

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

Foley, L.; Lin, J.T.S.; Weigele, M., 1978: Spectinomycin chemistry part 2 9 deoxy 4r di hydro spectinomycin and 9 deoxy spectinomycin. A [synthetic] route to 9-deoxyspectinomycin and 9-deoxy-4(R)-dihydrospectinomycin is described.

Foley, L.; Lin, J.T.S.; Weigele, M., 1978: Spectinomycin chemistry part 3 9 epi 4r di hydro spectinomycin and 9 epi spectinomycin. The preparation of 9-epi-4(R)-dihydrospectinomycin and of 9-epi-spectinomycin is described.

Foley, L.; Weigele, M., 1978: Spectinomycin chemistry part 1 characterization of a 5a 9a epi 4r di hydro spectinomycin derivative. The identification of a diastereomeric derivative of 4(R)-dihydrospectinomycin, having the reversed absolute stereochemistry in the cyclitol ring, is reported. The chemical transformations providing the unequivocal proof of a structure for this co...

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

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...

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