Process for the preparation of 1-N-isoseryl- or 1-N-(L-4-amino-2

Details Process for the preparation of 1-N-isoseryl- or 1-N-(L-4-amino-2 Process for the preparation of 1-N-isoseryl- or 1-N-(L-4-amino-2

1979-11-26

1981-05-19

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

424180, 536 17R, C07H 1522, A61K 3171

Patent

active

042686644

ABSTRACT:
1-N-Isoseryl- or 1-N-(L-4-amino-2-hydroxybutyryl)-3',4'-dideoxykanamycin B is prepared through a new route starting from 3',4'-dideoxy-3',4'-didehydrokanamycin B, which comprises the steps of protecting all or some of the four amino groups other than the 1-amino group of the starting material with an amino-protecting group, reacting the partially amino-protected derivative or derivatives thus formed with isoserine or L-4-amino-2-hydroxybutyric acid or a reactive derivative thereof having the amino group unprotected or protected whereby to acylate the 1-amino group of the former, eliminating the amino-protecting group or groups from the acylated product and reducing the 3',4'-olefinic double bond of the product by catalytic hydrogenation, the last two steps being effected in order or simultaneously or in the reverse order. Also provided are new, useful intermediate compounds during the process.

REFERENCES:
patent: Re28647 (1975-12-01), Umezawa et al.
patent: 3781268 (1973-12-01), Kawaguchi et al.
patent: 3939143 (1976-02-01), Umezawa et al.
patent: 4107424 (1978-08-01), Umezawa et al.
patent: 4156078 (1979-05-01), Umezawa et al.
patent: 4169939 (1979-10-01), Umezawa et al.

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