Spectinomycin modification. IV. 7-Deoxy-4(R)-dihydrospectinomycin.
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چکیده
منابع مشابه
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 bi...
متن کاملSpectinomycin 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 aminocyclitol ring provides valuable synthetic intermediates for the preparation of analogs of this important antibiotic. The new methodology provides an eff...
متن کاملModification of spectinomycin. 2. Derivatives of 4-dihydro-4-deoxy-4(R)-aminospectinomycin.
Acyl derivatives 5a approximately j and alkyl derivatives 7a approximately r of 4-dihydro-4-deoxy-4(R)-aminospectinomycin (1a) were prepared and tested for antibacterial activity. Only acyl compounds derived from long chain aliphatic acids showed activity in vitro, but were inactive when tested in vivo. All alkyl derivatives were active in vitro. In vivo however only the short chain derivatives...
متن کاملSpectinomycin 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 rearrangement of the 3'-S-isomer leads only to epoxide formation. Deprotection of the ring-expanded homolog gives homospectinomycin. The synthesis and biological activity ...
متن کامل(4R)-4-(Biphenyl-4-yl)-7-chloro-1,2,3,4-tetrahydroquinoline
The title compound, C(21)H(18)ClN, was synthesized by an enanti-oselective Brønsted acid-catalysed transfer hydrogenation reaction. The six-membered heterocycle adopts a half-chair conformation. It has the biphenyl residue in an axial position. The two rings of the biphenyl residue are almost coplanar [dihedral angle = 2.65 (9)°]. The crystal packing is stabilized by N-H⋯Cl hydrogen bonds, whic...
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ژورنال
عنوان ژورنال: The Journal of Antibiotics
سال: 1978
ISSN: 0021-8820,1881-1469
DOI: 10.7164/antibiotics.31.451