Method for the Stereoselective Synthesis of Phosphorus Compounds

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This patent describes a method for the stereoselective synthesis of phosphorus compounds, allowing for efficient and controlled production of chiral (non-racemic) phosphorus-based molecules. The technique involves attaching a chiral auxiliary to a phosphorus starting compound, reacting with a nucleophile, and finally removing the auxiliary, yielding products with high stereochemical purity. This method is particularly suitable for making chiral phosphates, phosphonates, and nucleoside-based prodrugs.

Use CasesContent extracted from patent full text and abstract with AI.

• Production of enantiomerically pure nucleoside phosphate prodrugs for antiviral or anticancer therapies.
• Manufacture of chiral phosphorus ligands for use in catalysis in organic synthesis and pharmaceutical manufacturing.
• Stereoselective preparation of phosphorus-containing agrochemicals for enhanced effectiveness and safety.
• Synthesis of P-chiral phosphin ligands used in metal-catalyzed asymmetric reactions in chemical industry.
• Development of advanced antisense oligonucleotides and modified therapeutic nucleic acids.
• Preparation of chiral phosphorus compounds as enzyme inhibitors (e.g., lipase or pepsin inhibitors) for biochemical research.

BenefitsContent extracted from patent full text and abstract with AI.

• Enables synthesis of highly pure (isomerically pure) chiral phosphorus compounds, essential for pharmaceuticals and fine chemicals.
• Improves atom economy and process efficiency compared to traditional separation or enzymatic methods.
• Simplifies regulatory approval for drugs by providing single stereoisomers rather than mixtures, reducing toxicity and side-effect risks.
• Broad applicability to different classes of phosphorus compounds (phosphates, phosphonates, amidates, etc.).
• Can be applied to large-scale synthesis due to readily available starting materials and suitable reaction conditions.
• Allows for selective and predictable introduction of desired stereochemistry at the phosphorus atom.

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Patent Abstract

The present invention relates to a method for the stereoselective synthesis of phosphorus compounds, wherein in the first reaction step a chiral auxiliary is covalently bound to the phosphorus atom of phosphoryl chloride, thiophosphoryl chloride or phosphorus trichloride, the product from the first reaction step in a subsequent step is reacted with an alcohol, thiol or amine as a nucleophile in the presence of a base, and in the last step the chiral auxiliary is displaced from the product of the subsequent step by a nucleophile.