L-talopyranoside derivatives and process for the preparation of

Details L-talopyranoside derivatives and process for the preparation of L-talopyranoside derivatives and process for the preparation of

1993-06-18

1994-12-20

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30902

Patent

active

053747461

ABSTRACT:
The present invention relates to a L-talopyranoside derivative of the formula (I): ##STR1## wherein, A is hydrogen atom, a lower alkyl group having 1 to 5 carbon atoms, or a hydroxyl-protecting group;
B.sub.1 and B.sub.2, the same or different from each other, are independently hydrogen atom or a hydroxyl-protecting group;
R.sub.1 and R.sub.2 may form a alkylene group with a carbon atom of 5-position of the sugar skeleton, or one of them is hydrogen atom and the other is CH.sub.2 X wherein, X is hydrogen, or a protected or un-protected hydroxyl group.
Provided that, the following compounds are excepted: ##STR2## wherein, B.sub.1 and B.sub.2 are independently hydrogen atom or acetyl. L-talopyronoside derivatives of the present invention is a very useful intermediate for the synthesis of anthracycline antibiotics having an antitumor activity. The process according to the invention has an advantage of significant reduction in the production cost and therefore expected to be very useful for the preparation of anthracycline antibiotics in an industrial scale.

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Raddo et al., Carbohydrate Research, 153, pp. 141-145, 1986.
Miura et al., The Journal of Antibiotics, 39(5), pp. 731-735, 1986.

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