C - Chemistry – Metallurgy – 07 – H
Patent
C - Chemistry, Metallurgy
07
H
260/230.58
C07H 15/26 (2006.01) C07H 17/04 (2006.01)
Patent
CA 2015072
- 1 - Abstract of the disclosure: HOE 89/B 015 A process for the preparation of glucosaminyl-epi-podo- phyllotoxin derivatives The invention relates to a novel process for the prepara- tion of glucosaminyl-epi-podophyllotoxin derivatives of the formula I Image I in which R1 is hydrogen or the acetyl or a mono-, di- or trihalo- genoacetyl protective group with halogen being fluor- ine, chlorine or bromine, R2 is hydrogen or (C1-C4)-alkyl, R3 hydrogen, (C1-C4)-alkyl or a benzyloxycarbonyl protective group, R4 is hydrogen, a mono-, di or trihalogenoacetyl pro- tective group, a benzyloxycarbonyl protective group or a methyl group, and A is C1-C4-alkyl, which comprises reacting a 3-0-acyl-2-N-benzyloxy- carbonyl-4,6-0-alkylidene-alpha-D-glucosamine derivative of the formula II, which is in the alpha-hydroxy form, Image II - 2 - in which R1 and R3 are acyl protective groups as defined above, and R2 is hydrogen, with a podophyllotoxin derivative of the formula III Image III in which R4 is a methyl group or a mono-, di- or trihalogenoacetyl or benzyloxycarbonyl protective group, in the presence of a promoter and of an anhydrous organic solvent at -50°C to 20°C to give a 4-O-(beta-glucosamin- yl)-epi-podophyllotoxin derivative of the formula I in which the radicals R1, R2, R3, and R4 retain their meaning as defined above, and subsequently converting the glyco- side products of the formula I, after elimination of the protective groups, into an amino or dialkylamino compound of the formula I.
Dehmel Konrad
Kolar Cenek
Behringwerke Aktiengesellschaft
Bereskin & Parr Llp/s.e.n.c.r.l.,s.r.l.
Dehmel Konrad
Kolar Cenek
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