99% Purity Ethyl (R)-4-cyano-3-hydroxybutyrate​ CAS 141942-85-0

1. Versatile Nitrile Functionality for Diverse Molecular Elaboration​

​Benefit:​​ The ​cyano (-CN) group is a highly versatile synthetic handle​ that can be cleanly transformed into a carboxylic acid, primary amine (via reduction), amide, or heterocycle (e.g., tetrazole). This enables a wider range of downstream transformations than the chloro group in the analogous chloride compound.

​Application Scenario:​​ In the ​synthesis of a novel GABAergic pharmaceutical candidate, medicinal chemists use this ester as the starting point. They first protect the alcohol, then reduce the nitrile to a primary amine, and finally cyclize it with the ester to form a chiral γ-lactam core structure—a transformation that is more direct and higher-yielding than routes requiring multiple steps from the chloride analog.

​2. Critical Chiral Precursor for Advanced Statin APIs​

​Benefit:​​ It is a ​key, stereospecific intermediate in the commercial synthesis of Rosuvastatin and other next-generation statins. The (R)-configuration at the hydroxy center is essential for optimal binding to the HMG-CoA reductase enzyme target.

​Application Scenario:​​ In the ​large-scale GMP manufacturing of Rosuvastatin Calcium, this compound is produced via a highly enantioselective biocatalytic reduction. It then undergoes a series of controlled reactions where the nitrile is selectively hydrolyzed to an acid and subsequently elaborated into the complete, pharmacologically active dihydroxy acid side chain with exceptional stereofidelity.

​3. Enables Efficient, Convergent Synthetic Strategies​

​Benefit:​​ The presence of three differentiable functional groups (ester, alcohol, nitrile) allows for ​sequential and orthogonal modifications. This facilitates convergent synthesis, where complex fragments can be assembled efficiently, saving steps and improving overall yield.

​Application Scenario:​​ During the ​research-phase synthesis of a complex natural product analog, chemists use this molecule as a central hub. They couple the acid derived from ester hydrolysis to one fragment via amide bond formation, while the nitrile is converted to a tetrazole bioisostere to interact with a specific enzyme pocket, rapidly generating a targeted library for screening from a single chiral source.

​4. Favorable Stability Profile for Process Chemistry​

​Benefit:​​ While still requiring careful handling, the ​cyano group is generally more stable toward displacement by weak nucleophiles than a chloro group​ under process conditions. This allows for greater flexibility in reaction sequence design and minimizes side reactions during the protection of the alcohol or manipulations of the ester.

​Application Scenario:​​ In a ​pilot plant synthesis, a reaction step requires heating in a polar aprotic solvent like DMF with a mild base. Using the cyano analog prevents the formation of elimination byproducts or ethers that could plague the process if the more labile chloro analog were used, leading to a cleaner reaction profile and simpler purification.

Ethyl (R)-4-Cyano-3-hydroxybutyrate (CAS 141942-85-0)​​ is a ​specialized, high-value chiral synthon​ whose advantage lies in its ​strategic nitrogen incorporation. It is not merely an alternative to the ubiquitous chloro analog but a deliberate choice for synthetic routes demanding the unique reactivity of the nitrile group. Its role as the ​preferred intermediate for Rosuvastatin​ underscores its industrial importance, while its three functional groups offer medicinal chemists a powerful toolkit for parallel diversification. For projects where the synthetic target lies "beyond the chloride"—requiring an amine, a tetrazole bioisostere, or other nitrogenous motifs—this compound provides the most efficient and stereocontrolled entry point, justifying its status as a premium building block in asymmetric synthesis.