tert-Butyl diethylphosphonoacetate

tert-Butyl diethylphosphonoacetate is a widely employed Horner‑Wadsworth‑Emmons reagent that enables the stereoselective construction of α,β‑unsaturated esters bearing a tert‑butyl protecting group. The key structural feature of tert-Butyl diethylphosphonoacetate is the diethyl phosphonate group, which upon deprotonation reacts with aldehydes and ketones to form α,β‑unsaturated esters with predictable (E)‑selectivity. tert-Butyl diethylphosphonoacetate is particularly valuable in total synthesis and complex molecule construction, as the diethyl phosphonate offers distinct reactivity and solubility profiles compared to the corresponding dimethyl phosphonate. Additionally, tert-Butyl diethylphosphonoacetate has been utilized as a reactant in the preparation of hydroxymethylated dihydroxyvitamin D₃ analogs via the Wittig‑Horner approach, as potential antitumor agents, and in the synthesis of phosphopeptide mimetic prodrugs targeted to the Src homology 2 (SH2) domain of signal transducer and activator of transcription 3 (Stat 3). The compound is also used in bicyclic triaminophosphine‑promoted stereoselective synthesis of α,β‑unsaturated esters, fluorides, and nitriles from aldehydes and ketones using Wadsworth‑Emmons phosphonates.

Product Parameters

Application

tert-Butyl diethylphosphonoacetate is used as biochemical reagents, pharmaceutical intermediates, etc.

Synthetic Route

Under nitrogen protection, triethyl phosphite (485 g) is placed in a three-neck round-bottom flask and heated to 90°C. At this temperature, tert-butyl bromoacetate (541 g) is slowly added dropwise over 2 hours. After the dropwise addition is completed, the reaction mixture is continuously stirred at 90°C for 4 hours. After the reaction is finished, the mixture is cooled to room temperature. The low-boiling components are removed by vacuum distillation to obtain the colorless liquid product tert-butyl diethylphosphonoacetate (680 g, yield 97%), which has a purity of >98% as analyzed by gas chromatography.

Why Cosperpharm?

When your total synthesis or medicinal chemistry program requires reliable Horner‑Wadsworth‑Emmons reagents with documented purity and traceability, Cosperpharm delivers tert-Butyl diethylphosphonoacetate with the quality and supply chain reliability that research chemists expect.

Quality assurance. Every batch of tert-Butyl diethylphosphonoacetate undergoes analytical release testing including GC purity verification and physical property confirmation. Each batch receives a unique lot number with full traceability.

Documentation for your research. Cosperpharm supplies tert-Butyl diethylphosphonoacetate with comprehensive Certificates of Analysis (COA) and Safety Data Sheets (SDS).

Flexible supply. Cosperpharm supplies tert-Butyl diethylphosphonoacetate from gram-scale research quantities to larger batches for process development. R&D samples ship within 5–7 business days.

Technical expertise. Our team can advise on HWE reaction conditions and phosphonate chemistry.

Global logistics. Cosperpharm ships worldwide with full customs documentation included.

Contact Us

Looking for a reliable source of tert-Butyl diethylphosphonoacetate for your HWE olefination reactions or total synthesis program? Cosperpharm is ready to support your project.