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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

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