Method for the preparation of 4'-0-tetrahydropyranyladriamycin b

Details Method for the preparation of 4'-0-tetrahydropyranyladriamycin b Method for the preparation of 4'-0-tetrahydropyranyladriamycin b

1986-10-30

1989-04-04

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

C07H 1524

Patent

active

048188182

ABSTRACT:
For the preparation of 4'-0-tetrahydropyranyladriamycin b, the 9,14-position of the starting adriamycin is previously protected with phenylboronic acid and then the 4'-position of the thus protected adriamycin is selectively tetrahydropyranylated. After the tetrahydropyranylation, the by-product of 4'-0-tetrahydropyranyladriamycin a is converted to the aimed product of 4'-0-tetrahydropyranyladriamycin b. The yield of the product of 4'-0-tetrahydropyranyladriamycin b is high.
The present invention provides a method for the preparation of 4'-0-tetrahydropyranyladriamycin b, where 3,4-dihydro-2H-pyran is added to a reaction solution containing a 9,14-protected adriamycin as obtained by (a) reacting adriamycin and phenyl-boronic acid or (b) reacting 4'-0-tetrahydropyranyladriamycin b and phenylboronic acid in the presence of an acid catalyst, for 4'-tetrahydropyranylation of the said 9,14-protected adriamycin, and then, the 9,14-protected position of the resulting product is deprotected and 4'-0-tetrahydropyranyladriamycin b is isolated by chromatography with silica-gel.

REFERENCES:
patent: 4360664 (1982-11-01), Umezawa et al.

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