Title: Improved process for the preparation of 4-demethoxy-daunorubicin
Application Number: 85103835 Application Date: 1985.05.13
Publication Number: 1004868 Publication Date: 1986.11.12
Approval Pub. Date: Granted Pub. Date:
International Classifi-cation: A61K31/70,C07H15/24
Applicant(s) Name: Farmitalia Carlo Erba S.P.A. (IT) Via C. Imbonati, Address:
Inventor(s) Name: Federico Arcamone
Attorney & Agent: TIANG YUE MU DEJUN
Abstract:
     An improved process for preparation of 4-demethoxy-daunorubicin. hydrochloric acid (1) was discribed. A 4-demethoxy-daunorubicinone having optical activity as the starting subsfance for the process is made to conduct a condensation reaction with N,O-trifluoroacetyl-protected 1-chloro-daunoamine in a suitable organic solvent in the presence of silver trifluoromethylsulfonate to yield N,O-trifluoroacetyl-protected glycoside having the isostructure with alpha-terminal group, which is first treated with methanol to remove one of the protecfing groups, and then a mild alkaline hydrolysis is carried out in a dilute aqueous solution of sodium hydroxide to give a free glycoside base of (1), which is finally converted into its corresponding hydrochloric acid salt and separated.
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