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Spectinomycin chemistry part 1 characterization of a 5a 9a epi 4r di hydro spectinomycin derivative

Journal of Organic Chemistry 43(22): 4355-4359

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 compound take advantage of the instability of the diastereomeric skeleton relative to that of spectinomycin.

Accession: 006459318

Related references

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.; 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.

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.

Foley, L.; Lin, J.T.; Weigele, M., 1978: Spectinomycin chemistry. III.9-EPI-4(R)-dihydrospectinomycin and 9-epi-spectinomycin. Journal of Antibiotics 31(10): 985-990

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

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Yu, G.C.eng; Wang, J.H.a; Shao,, 1994: Selection of spectinomycin resistant, high yielding spectinomycin producing strains. The spore suspension of the spectinomycin producing mutant No. 47-4 after treatment by combination of lithium chloride and ultraviolet light, was selected on the gradient plates containing 5000 mu-g/ml spectinomycin in Gause No. 1 medium. It was p...

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...

Hanley, J.E.; Davis, R.B.; Sunka, E.M., 1968: An evaluation and comparison of spectinomycin and spectinomycin-erythromycin combinations for infectious coryza. A comparison and evaluation was made of Spectinomycin and of Spectinomycin-erthromycin combinations in the treatment of infectious coryza in chickens under simulated field conditions. The drugs appeared to be of value in the treatment, with Specti...