Trademarks: Crestor; Zyrova
Molecular Formula: C22H28FN3O6S
CAS Registry Number: 287714-41-4
CAS Name: (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid
Molecular Weight: 481.539
SMILES: CC(C)C1=NC(=NC(C2=CC=C(F)C=C2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(=O)O)N(C)S(C)(=O)=O
InChI Key: BPRHUIZQVSMCRT-VEUZHWNKSA-N
InChI: InChI=1S/C22H28FN3O6S/c1-13(2)20-18(10-9-16(27)11-17(28)12-19(29)30)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)33(4,31)32/h5-10,13,16-17,27-28H,11-12H2,1-4H3,(H,29,30)/b10-9+/t16-,17-/m1/s1
Activity: Hydroxymethylglutaryl-CoA Reductase Inhibitors; HMG-CoA inhibitor
Status: Launched 2003
Originator: Shionogi/Merck
Rosuvastatin synthesis: EP0521471B1 (also Ref. 2)
Rosuvastatin synthesis: Starting material [Beilstein J Org Chem 2013, 9, 2265–2319 (also Ref. 4)]
Rosuvastatin synthesis: Side Chain [J Org Chem 1994 59(25), 7849-7854]
Rosuvastatin synthesis: Int J Pharm Biomed Sci 2013, 4(4), 118-121
1. Watanabe, M.; et. al. Pyrimidine derivatives as HMG-CoA reductase inhibitors. EP0521471B1
2. Watanabe, M.; et. al. Synthesis and Biological Activity of Methanesulfonamide Pyrimidine- and N-Methanesulfonyl Pyrrole-Substituted 3,5-Dihydroxy-6-heptenoates, a Novel Series of HMG-CoA Reductase Inhibitors. Bioorg Med Chem 1997, 5(2), 437-444.(Many texts give a wrong citation with BMCL instead of BMC)
3. Baumann, M.; et. al. An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles. Beilstein J Org Chem 2013, 9, 2265-2319.
4. Börner, A.; et. al. A New Approach to the Total Synthesis of Rosuvastatin. Eur J Org Chem 2008, 5, 847-853.
5. Patil, P. B.; et. al. An efficient scalable process for rosuvastatin calcium. Int J Pharm Biomed Sci 2013, 4(4), 118-121.
6. Konoike, T.; et. al. Practical Synthesis of Chiral Synthons for the Preparation of HMG-CoA Reductase Inhibitors. J Org Chem 1994, 59(25), 7849-7854.
