Process for the production of kanomycin B derivatives and produc

Details Process for the production of kanomycin B derivatives and produc Process for the production of kanomycin B derivatives and produc

1980-10-14

1982-09-14

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

424180, 536 137, C07H 1522

Patent

active

043496660

ABSTRACT:
3'-Deoxykanamycin B, namely tobramycin is produced in an improved yield with a reduced reaction time under moderate reaction conditions, starting from a penta-N-protected 3'-mono-O-alkyl-, aralkyl- or arylsulfonylated derivative of kanamycin B in which all the 1, 3, 2' and 3"-amino groups and possibly the 6'-amino group have been protected by an arylsulfonyl group, especially tosyl group; the 3'-hydroxyl group of kanamycin B has been alkyl-, aralkyl- or arylsulfonylated; the 4"- and 6"-hydroxyl groups have been blocked with a di-valent hydroxyl-protecting group; and possibly the 4'-hydroxyl group and 6'-amino group have been blocked by being converted into the form of a 4', 6'-cyclic carbamate formed between the 4'-hydroxyl group and the 6'-amino group, by subjecting to a process essentially comprising reaction of said protected kanamycin B derivative with a metal halide for a reaction time of 30 min. to 2 hours at a reaction temperature of 0.degree. C..about.150.degree. C. to produce the corresponding 3'-halo compound, reductive replacement of the 3'-halo group by hydrogen and deprotection.

REFERENCES:
patent: Re28647 (1975-12-01), Umezawa et al.
patent: 3929762 (1975-12-01), Umezawa et al.
patent: 4125706 (1978-11-01), Umezawa et al.
patent: 4156078 (1979-05-01), Umezawa et al.
patent: 4195170 (1980-03-01), Umezawa et al.

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