3',4'-Diedeoxykanamycin B derivatives

Details 3',4'-Diedeoxykanamycin B derivatives 3',4'-Diedeoxykanamycin B derivatives

1980-09-15

1982-11-02

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

424180, 536 137, A61K 3171, C07H 1522

Patent

active

043574653

ABSTRACT:
New routes are provided for the synthesis of 3',4'-dideoxykanamycin B which is effective in inhibiting kanamycin-resistant organisms from kanamycin B through new intermediate, of which a fundamental process comprises a new reaction of a 3',4'-epoxy derivative of amino- and hydroxyl-protected kanamycin B with a xanthate to form a corresponding 3',4'-dideoxy-3'-eno derivative followed by removal of the amino- and hydroxyl-protecting groups thereof and by hydrogenation of the resulting 3',4'-dideoxy-3'-eno-kanamycin B. A 3',4'-episulfide derivative corresponding to the 3',4'-epoxy derivative which is formed as second product in the reaction of 3',4'-epoxy derivative with xanthate is also used as intermediate for the preparation of 3',4'-dideoxykanamycin B.

REFERENCES:
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patent: 4060682 (1977-11-01), Umezawa et al.
Tipson, "Advances in Carbohydrate Chem. and Biochem.", vol. 25, 1970, pp. 134-141, Academic Press, New York.
Kojima et al., "Tetrahedron Letters", No. 7, 1968, pp. 839-842.
Umezawa et al., "Jour. of Antibiotics", vol. XXIV, No. 7, 1971, pp. 485-487.
Umezawa et al., "Jour. of Antibiotics", vol. XXV, No. 12, 1972, pp. 743-745.
Umezawa et al., "Bulletin of the Chem. Soc. of Japan", vol. 45, 1972, pp. 3624-3628.
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