C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 473/00 (2006.01) C07C 35/06 (2006.01) C07C 43/13 (2006.01) C07C 69/96 (2006.01) C07D 239/46 (2006.01) C07D 239/54 (2006.01) C07D 319/06 (2006.01) C07D 319/08 (2006.01) C07D 327/06 (2006.01) C07D 327/10 (2006.01) C07D 471/04 (2006.01) C07D 487/04 (2006.01) C07F 7/08 (2006.01) C07F 7/18 (2006.01) C07F 9/547 (2006.01) C07F 9/6571 (2006.01) C07F 9/6574 (2006.01)
Patent
CA 2082552
FL/6- 18845/A Process for the preparation of carbacyclic nucleosides, and intermediates ABSTRACT Process for the preparation of racemic compounds of the formula I Image (I), or enantiomers thereof, in which B is the radical of a nucleic base from the series comprising purine, a purine analogue or a pyridine analogue, and R is H or a protective group R1, by reacting a) a compound of the formula II or enantiomer thereof Image (II), with a compound of the formulae X-CO-X, X-CS-X, X-SO-X, X-SO2-X, R2-NCO, R3R4N-C(O)-R5, X2P-R6 or X2P(O)-R6, in which X is a leaving group, R2 is, for example, C1-C18alkyl, R3 and R4 are, for example, H or C1-C18alkyl, R5 is, for example, H or C1-C12alkyl, and R6 is, for example, C1-C12alkyl or C1-C12alkoxy, to give a compound of the formula III or enantiomers thereof Image (III), in which Y is the groups -C(O)-, -C(S)-, -SO-, -SO2-, R2NH-CH=, R3R4N-CR5=, R6P=and R6(O)P=; b) the further reaction of the compounds of the formulae III or enantiomers thereof with a nucleic base B on its own or together with a non-nucleophilic base, or with an alkali metal salt of the nucleic base B, to give compounds of the formula IV or enantiomers thereof Image (IV), in which M is H, an alkali metal or a non-nucleophilic base, and c) the conversion of the compounds of the formulae IV into the compounds of the formulae I by elimination of the protective group R1 and of the group YOM. The reaction b) is regioselective and diastereoselective, and the compounds of the formula I are obtained in high yields and purities.
Fetherstonhaugh & Co.
Novartis Ag
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