Process for preparing daunomycin and analogues thereof

Details Process for preparing daunomycin and analogues thereof Process for preparing daunomycin and analogues thereof

1976-08-14

1978-08-15

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

260365, 536 17, C07H 1524

Patent

active

041074238

ABSTRACT:
Racemic anthracyclinones of the general formula II ##STR1## when condensed with 2,3,6-trideoxy-3-trifluoroacetamido-4-0-trifluoroacetyl-.alpha.-L-lyxo-pyr anosyl chloride in the presence of silver trifluoromethane sulphonate yield an easily separable mixture of equimolar amounts of exclusively the .alpha.-glycoside of the 7S : 9S diastereomer and the .beta.-glycoside of the 7R : 9R diastereomer. In this way the biologically important .alpha.-glycosides of the 7S : 9S diastereomer of the general formula I (below) are easily prepared from a racemic anthracyclinone.

REFERENCES:
patent: 3427300 (1969-02-01), Sarett et al.
patent: 3590028 (1971-06-01), Arcamone et al.
patent: 3629231 (1971-12-01), Hough et al.
patent: 3665018 (1972-05-01), Jolles et al.
patent: 3803124 (1974-04-01), Arcamone et al.
patent: 4039663 (1977-08-01), Arcamone et al.

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