ICIC 2014 New Product Introduction Wiley

1. Synthesis Planning With Wiley’s Chemistry Toolkit
Orr Ravitz
wileysciencesolutions.com

2. The Vision
Turn:
information into knowledge,
answers for questions into solutions for problems

3. How can I make my target molecule:
Quickly
Efficiently
Cheaply
From building blocks available in batch quantities
Using scalable methods (techniques, conditions…)
With low environmental footprint
How can I make a series of compounds?
Synthesis Challenges
Discovery
Development
Process

4. Knowledge
Intuition
Experience
How do we approach the problem now?
Standard literature mining:
Has this been made before?
Any similar structures?
How can I accomplish this transformation that I have in mind?
Step-by-step analysis

5. Computer-Aided Synthesis Design
The Approach:
Comprehensive rule- and precedent-based retrosynthetic analysis back to available starting materials.
Automated rule generation with manual rule curation.
Generate many alternatives.
Provide supporting literature examples.
Allow user guidance and control.

6. Rule Extraction
Source reactions
Esterification examples
Other examples
··· → ···
··· → ···
··· → ···
Esterification rule
Other rule
··· → ···
Reactions
Reaction Rules

7. Chemical Perception
Identify essential chemical environment and compatible functional groups
?
?
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Regioselectivity
Stereochemistry

8. Synthetic Routes

9. Alternative Paths

10. Literature Examples

13. CIRX and CASD
Detail:
Chemoselectivity (including 0% yield reactions)
Stereochemistry:
Stereodescriptors, (+)-I, (±)-I, (R)-I, (S)-(-)-I
Selectivity: e.e., d.e. ds and also E:Z>95:5, α:β=1:3
Labelling of asymmetrical centers (R,S)
Meta data: conditions, solvents, catalysts, bibliography
Accuracy and consistency:
Mapping
Attention to details
Very high quality assurance
Uniformly across DB

14. An Integrated Solution
Data mining and synthesis planning in one tool.
Use the most suitable data source for predictions (CIRX)
Develop the data source to address the needs of the chemists
Offer a gateway to the users’ own data fully behind the firewall.
Integrate/ interact with other data sources
Interact with other tools
Use the system to generate and share knowledge
Become involved!