Method for the synthesis of (2"R)-4'-O-tetra-hydropyranyladriamy

Details Method for the synthesis of (2"R)-4'-O-tetra-hydropyranyladriamy Method for the synthesis of (2"R)-4'-O-tetra-hydropyranyladriamy

1988-06-09

1989-12-26

Schofer, Joseph L.

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

Organic compounds

Carbohydrates or derivatives

C07H 1524

Patent

active

048899267

ABSTRACT:
A new compound, i.e., 14-chlorodaunomycin, and its method of preparation are provided. The new compound, useful as an antitumor agent and as an intermediate in the preparation of (2"R)-4'-O-tetrahydropyranyladriamycin, is obtained by reaction of daunomycin with an alkyl ortho-formate and a brominating agent to produce a 14-bromo-13-dialkylketaldaunomycin, hydrolysis of the latter compound, then adding an excess of a solid metal/chloride to produce an acid addition salt of 14-chlorodaunomycin and concurrently salting out the latter compound from the reaction solution, followed by recovering the 14-chlorodaunomycin acid addition salt.

REFERENCES:
patent: 4818818 (1989-04-01), Umezawa et al.

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