C - Chemistry – Metallurgy – 07 – H
Patent
C - Chemistry, Metallurgy
07
H
260/233.3
C07H 15/26 (2006.01) C07H 17/04 (2006.01)
Patent
CA 2015074
- 1 - BEHRINGWERKE AKTIENGESELLSCHAFT HOE 89/B 014 - Ma 763 Dr. Ha/Sd Abstract of the disclosure A process for the preparation of etoposides The invention relates to a process for the preparation of a beta-glucopyranose derivative of the formula I Image I in which R1 and R2 are H or an acyl protective group and R3 is H, benzyl or a radical of the formula II Image II with R4 being H or a benzyloxycarbonyl or chloroacetyl protective group and A being C1-C4-alkyl, which comprises eliminating the benzyl group in a benzylglucopyranoside of the formula I in which R1 and R2 are an acyl protective group, R3 is a benzyl protective group and A is C1-C4-alkyl, by hydrogenolysis in the presence of a hydrogenation catalyst and of an organic solvent, there being formation of a glucopyranose derivative of the formula I which is in the beta-hydroxy form and in which R1, R2 and A retain their meaning, and R3 is a hydrogen atom, subsequently reacting this glycosi- dation component with an epi-podophyllotoxin derivative of the formula III Image III in which R4 is benzyloxycarbonyl or chloroacetyl protective group, in the presence of a promoter such as, preferably, BF3.ether or of a tri-(C1-C4)-alkylsilyl trifluorome- thanesulfonate and of an organic solvent, where appro- priate in the presence of a desiccant at -30°C to 0°C, there being formation of a beta-glycoside of the formula I in which R1, R2, R4 and A retain their meaning, and R3 is a radical of the formula II, and eliminating in a product which is formed the benzyloxycarbonyl protective group by hydrogenolysis and the acyl protective group using basic ion exchangers in the presence of a polar solvent, there being formation of a product of the formula I in which R1 and R2 are hydrogen, R3 is a radical of the formula II with R4 equal to hydro- gen, and A is C1-C4-alkyl.
Behringwerke Aktiengesellschaft
Bereskin & Parr Llp/s.e.n.c.r.l.,s.r.l.
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