Trehalose-Based DATH Synthesis Through Protected Intermediates
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Solution Overview
Problem
Existing methods for producing 6,6′-diamino-6,6′-deoxy-trehalose (DATH) are inefficient and lack a cost-effective process using trehalose as a starting material.
Innovation Solution
A method involving the protection and replacement of hydroxyl groups in trehalose to form intermediates, followed by conversion to DATH or its salts, utilizing protecting groups like 4-nitrobenzenesulfonyl and potassium phthalimide, benzyl amine, or azides, with optional steps for purification.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If existing methods are used to produce DATH, then production can occur, but the process is inefficient and lacks cost-effectiveness
Solution Approach 1:
The patent applies preliminary action by protecting hydroxyl groups of trehalose before performing substitution reactions. Specifically, hydroxyl groups are protected with protecting groups (such as silyl ethers, esters, or ethers) in advance to prevent unwanted side reactions during subsequent steps with reagents like halogenating agents or azides. This preliminary protection enables more efficient and selective production of DATH intermediates, improving overall productivity while reducing waste and cost.
2Manufacturing precision
If hydroxyl groups are protected and replaced through multiple steps, then DATH can be produced with control, but the process complexity increases
Solution Approach 1:
The patent applies segmentation by dividing the DATH synthesis into distinct modular steps: (1) protection of hydroxyl groups with specific protecting groups, (2) substitution of protected hydroxyl groups with halogenating agents to form halide intermediates, (3) replacement of halides with azides or protected amines, and (4) final deprotection to yield DATH. Each step is independently optimized and controlled, enabling precise manufacturing while maintaining manageable process complexity through clear separation of functions.
Solution Approach 2:
The patent uses intermediary compounds (protected trehalose derivatives, halide intermediates, azide intermediates) as mediators between the starting material trehalose and the final product DATH. These intermediaries enable controlled transformation at each stage, allowing precise manipulation of functional groups while simplifying the overall process by breaking down complex transformations into manageable sequential steps with well-defined intermediates.
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 enables the efficient production of DATH or its salts from trehalose, providing a cost-effective and controlled synthesis pathway.
Implementation Method 1
reacting primary hydroxyl groups at carbon 6 of each monosaccharide of the D-trehalose or the D-trehalose derivative and 4-nitrobenzenesulfonyl-LG to provide intermediate 1A comprising 4-nitrobenzenesulfonyl hydroxyl protected groups
Implementation Method 2
reacting the primary hydroxyl groups of the D-trehalose or the D-trehalose derivative and a halogen to provide intermediate 1B comprising halide groups
Implementation Method 3
replacing the halides with protected amines or with azides to provide intermediate 2
Implementation Method 4
reacting the 4-nitrobenzenesulfonyl hydroxyl protected groups and potassium phthalimide, benzyl amine, ammonia, or NaN3 to provide intermediate 2A
Implementation Method 5
converting the intermediate 2 to DATH or a salt thereof
Data Source
AI summary
The present technology is direct to methods of producing 6,6′-diamino-6,6′-deoxy-trehalose (“DATH”) or a salt thereof. The methods include optionally protecting one or more hydroxyl groups of D-trehalose and converting the primary hydroxyl groups of D-trehalose to product DATH or a salt thereof through use of a halogen, azide, and/or protected amine to. The present technology is also direct to intermediate products of the methods.