Comprehensive synthesis planning using multiple reaction search algorithms

CINF 74

Valentina Eigner-Pitto, ve@infochem.de1, Josef Eiblmaier1, Hans Kraut1, Heinz Saller1, Peter Loew1, and Guenter Grethe, ggrethe@comcast.net2. (1) InfoChem GmbH, Landsberger Strasse 408, Munich, 81241, Germany, (2) Consultant, 352 Channing Way, Alameda, CA 94502-7409
InfoChem's approach to computer based synthesis design integrates various tools and algorithms to support the synthetic chemist in finding the optimal synthesis route to target molecules. Established search modes such as reaction substructure and role searching are enhanced by innovative algorithms such as reaction type and name reaction searching. A new retrosynthetic approach based on automatic transform library generation will be presented. A key innovation is that reaction classification allows a proposed retrosynthesis to be verified against databases of known chemical reactions. Our classification categorizes reactions according to the type of chemical transformation they represent. The resulting reaction "ClassCodes" are used to find and to interlink reactions having the same reaction type across large reaction databases. Synthetic routes can be further refined by name reaction filtering. The name reactions are organized in hierarchical order from main categories (addition, rearrangements, etc.) down to highly specific reaction variants (e.g., “Diels-Alder reaction”).