Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein
The present invention relates to processes for preparing the compounds of general formula I, wherein the groups R 1 and R 3 are defined according to claim 1 . Furthermore this inventions relates to intermediates obtained in these processes.
1. Process for preparing the compounds of general formula II,
wherein
R 1 denotes R-tetrahydrofuran-3-yl or S-tetrahydrofuran-3-yl; and
R 2 independently of one another denote hydrogen, (C 1-18 -alkyl)carbonyl, (C 1-18 -alkyl)oxycarbonyl, arylcarbonyl, aryl-(C 1-3 -alkyl)-carbonyl, aryl- C 1-3 -alkyl -alkyl, allyl, R a R b R c Si, or CR a R b OR c , wherein two adjacent groups R 2 may be linked with each other to form a bridging group SiR a R b , CR a R b or CR a OR b —CR a OR b ;
R a , R b , R c independently of one another denote C 1-4 -alkyl, aryl or aryl-C 1-3 -alkyl, while the alkyl groups may be mono- or polysubstituted by halogen;
L1 independently of one another are selected from among fluorine, chlorine, bromine, C 1-3 -alkyl , C 1-4 -alkoxy and nitro;
while by the aryl groups mentioned in the definition of the above groups are meant phenyl or naphthyl groups, which may be mono-or polysubstituted with L1;
said method comprised of the steps of reacting a glucose derivative of the formula XXXV
wherein R 2 is defined as hereinbefore and
Hal denotes F, Cl, Br, C 1-3 -alkylcarbonyloxy, C 1-3 -alkyloxycarbonyloxy or C 1-3 -alkyloxy;
with a metallated aglycon of the formula VI
wherein R 1 is defined as hereinbefore and M denotes a zinc moiety;
to yield the product of the formula II.
2. The process according to claim 1 , wherein R 2 independently of one another denote C 1-4 -alkylcarbonyl, C 1-4 -alkyloxycarbonyl, arylmethyl or R a R b R c Si.