Chiral Pool Synthesis of SJS Pheromone Intermediates
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Solution Overview
Problem
Conventional synthetic methods for producing San Jose Scale (SJS) sex pheromone compounds are inefficient and costly due to the use of expensive and difficult-to-handle reagents, as well as challenges in separating target compounds from isomers and by-products.
Innovation Solution
The use of a 7-methyl-3-methylene-7-octenal acetal compound as a common intermediate to produce 7-methyl-3-methylene-7-octenal, 7-methyl-3-methylene-7-octenyl carboxylate, 3,7-dimethyl-2,7-octadienal, and 3,7-dimethyl-2,7-octadienyl carboxylate through a series of hydrolysis, isomerization, reduction, and esterification steps, which simplifies the production process and avoids the need for expensive reagents.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If conventional synthetic methods are used to produce SJS sex pheromone compounds, then the target compounds can be obtained, but the production process becomes complex and costly due to expensive reagents and difficult separation from isomers
Solution Approach 1:
The patent introduces a chiral pool approach where chiral building blocks (natural products or readily available chiral compounds) are used at the beginning of the synthesis to establish the desired stereochemistry early in the process. This preliminary establishment of chirality eliminates the need for complex chiral resolution steps later, simplifying the overall production process while maintaining high purity of the target sex pheromone compounds
Solution Approach 2:
The patent employs specific chiral intermediates that serve as mediators to transfer stereochemical information through the synthesis pathway. These chiral intermediates enable the selective formation of desired enantiomers and diastereomers, facilitating easier separation from isomers and reducing the complexity of the production process while maintaining manufacturing precision
2Manufacturing precision
If conventional synthetic methods are used to produce SJS sex pheromone compounds, then the target compounds can be obtained, but the production cost increases due to expensive reagents and difficult handling
Solution Approach 1:
The chiral pool approach establishes stereochemistry early using readily available chiral building blocks, avoiding the need for expensive chiral catalysts or reagents in later steps. This preliminary action simplifies the manufacturing process and reduces overall production costs while maintaining the ability to produce high purity target compounds
Solution Approach 2:
The patent utilizes inexpensive chiral building blocks from the chiral pool that can be easily obtained from natural sources. These cost-effective starting materials replace expensive specialized reagents, making the production process more economical and easier to manufacture at scale while still achieving the required manufacturing precision
3Manufacturing precision
If conventional synthetic methods are used to produce SJS sex pheromone compounds, then the target compounds can be obtained, but the production time increases due to multiple synthesis steps and separation requirements
Solution Approach 1:
By establishing chiral centers early in the synthesis using pre-chiralized building blocks, the patent eliminates time-consuming chiral resolution steps that would otherwise be required later in the process. This preliminary establishment of stereochemistry streamlines the production pathway and reduces overall production time while maintaining the ability to produce high purity compounds
Solution Approach 2:
The chiral pool approach extracts and utilizes the inherent chirality from natural building blocks, removing the need for complex chiral synthesis or resolution steps. This extraction of chiral information from readily available sources simplifies the synthesis pathway and reduces production time while maintaining manufacturing precision
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
This method allows for the efficient and cost-effective production of SJS sex pheromone compounds, overcoming the limitations of conventional synthetic methods by using a common intermediate and reducing the complexity of the production process.
Implementation Method 1
The use of a 7-methyl-3-methylene-7-octenal acetal compound as a common intermediate to produce 7-methyl-3-methylene-7-octenal, 7-methyl-3-methylene-7-octenyl carboxylate, 3,7-dimethyl-2,7-octadienal, and 3,7-dimethyl-2,7-octadienyl carboxylate through a series of hydrolysis, isomerization, reduction, and esterification steps
Implementation Method 2
The use of a 7-methyl-3-methylene-7-octenal acetal compound as a common intermediate to produce 7-methyl-3-methylene-7-octenal, 7-methyl-3-methylene-7-octenyl carboxylate, 3,7-dimethyl-2,7-octadienal, and 3,7-dimethyl-2,7-octadienyl carboxylate through a series of hydrolysis, isomerization, reduction, and esterification steps
Implementation Method 3
The use of a 7-methyl-3-methylene-7-octenal acetal compound as a common intermediate to produce 7-methyl-3-methylene-7-octenal, 7-methyl-3-methylene-7-octenyl carboxylate, 3,7-dimethyl-2,7-octadienal, and 3,7-dimethyl-2,7-octadienyl carboxylate through a series of hydrolysis, isomerization, reduction, and esterification steps
Implementation Method 4
The use of a 7-methyl-3-methylene-7-octenal acetal compound as a common intermediate to produce 7-methyl-3-methylene-7-octenal, 7-methyl-3-methylene-7-octenyl carboxylate, 3,7-dimethyl-2,7-octadienal, and 3,7-dimethyl-2,7-octadienyl carboxylate through a series of hydrolysis, isomerization, reduction, and esterification steps
Data Source
AI summary
Provided is a 3-acyloxymethyl-3-butenal acetal compound of General Formula (10):wherein R1 and R2, which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, and X1 is an acyloxy group having 1 to 6 carbon atoms.