Polyol-Derived Compounds High BHB Content Synthesis
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Solution Overview
Problem
Existing methods for synthesizing acetoacetylated polyalcohols and β-hydroxy butyric acid (BHB) esters of polyalcohols suffer from poor atom economy and result in low BHB content per polyalcohol unit, limiting their efficiency in delivering BHB for therapeutic applications.
Innovation Solution
The process involves reacting a polyol or a β-hydroxyl butyric acid ester of a polyol with diketene, followed by hydrogenation and optional esterification, to produce compounds with a high BHB unit or acetoacetate concentration per polyalcohol unit, thereby enhancing BHB delivery efficiency.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Quantity of substance
If conventional coupling methods are used to synthesize BHB esters of polyalcohols, then the synthesis can proceed with standard reagents, but the atom economy is poor and BHB content per polyalcohol unit is low
Solution Approach 1:
The patent changes the chemical parameters of the synthesis by using diketene instead of conventional protected beta hydroxy butyric acid or acetoacetate esters. This reagent substitution enables direct formation of BHB esters with high BHB content per polyalcohol unit while improving atom economy, as diketene adds acetoacetate groups efficiently without requiring protecting group chemistry
Solution Approach 2:
The invention extracts and eliminates the unnecessary protecting group steps from the conventional synthesis pathway. By using diketene directly, the method removes the need for protection and deprotection cycles, thereby improving atom economy and increasing the effective BHB content per polyalcohol unit
2Adaptability or versatility
If BHB units are protected in BHB esters of polyalcohols, then further BHB precursors can be delivered upon hydrolysis, but the synthesis process becomes more complex
Solution Approach 1:
The patent applies preliminary action by incorporating protected BHB units during the initial synthesis step using diketene. The protecting groups are installed in advance on the BHB units, enabling subsequent hydrolysis to release additional BHB precursors. This preliminary functionalization occurs during the main coupling reaction rather than requiring separate protection steps
Solution Approach 2:
The synthesized BHB esters of polyalcohols serve multiple functions: they provide immediate BHB content, contain protected BHB units that can be hydrolyzed to release additional BHB precursors, and maintain structural integrity for parenteral nutrition applications. The diketene-derived acetoacetate groups serve both as BHB sources and as protectable functional handles
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 achieves improved atom economy and cost efficiency, allowing for the synthesis of polyalcohols with a high BHB unit content per polyol unit, which is beneficial for therapeutic applications.
Implementation Method 1
reacting a polyol or a β-hydroxyl butyric acid ester of a polyol with diketene
Implementation Method 2
subsequent hydrogenation
Data Source
AI summary
The present invention relates to polyol-derived compounds and processes preparing the same.