Synthesis Planning With Wiley’s Chemistry Toolkit

Orr Ravitz

wileysciencesolutions.com

The Vision

Turn:

information into knowledge,

answers for questions into solutions for problems

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

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

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.

Rule Extraction

Source reactions Esterification examples

Other examples

··· → ··· ··· → ··· ··· → ···

Esterification rule

Other rule

··· → ···

Reactions

Reaction Rules

Chemical Perception Identify essential chemical environment and compatible functional groups

? ? ? Regioselectivity

Stereochemistry

Synthetic Routes

Alternative Paths

Literature Examples

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

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!