55429-66-8

Usage

Uses

Used in Organic Synthesis:
(4R)-1-(Trimethylsilyl)-4-(trimethylsiloxy)-L-proline trimethylsilyl ester serves as a protecting group for the carboxyl group of amino acids, which is crucial for preventing unwanted reactions during complex organic synthesis processes.
Used in Pharmaceutical Preparation:
(4R)-1-(Trimethylsilyl)-4-(trimethylsilyloxy)-L-proline trimethylsilyl ester acts as a chiral building block in the preparation of pharmaceuticals, contributing to the development of enantiomerically pure drugs, which is essential for ensuring the desired therapeutic effects and minimizing side effects.
Used in Agrochemical Production:
(4R)-1-(Trimethylsilyl)-4-(trimethylsiloxy)-L-proline trimethylsilyl ester is also utilized as a chiral building block in the synthesis of agrochemicals, aiding in the creation of effective and selective pesticides or other agricultural products.

Upstream product

• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 596817-06-0 (2S,4S)-1-(2-chloroacetyl)-4-fluoropyrrolidine-2-carbonitrile 
• 596817-05-9 (2S,4S)-N-chloroacetyl-4-fluoropyrrolidine-2-carboxamide 

Relevant academic research and scientific papers

4-fluoropyrrolidine-2-carbonyl fluorides: Useful synthons and their facile preparation with 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride

4-Fluoropyrrolidine derivatives are useful in medicinal chemistry applications such as dipeptidyl peptidase IV inhibitors. As attractive synthons for these, N-protected (2S,4S)-4-fluoropyrrolidine-2-carbonyl fluorides were synthesized in high yield by double fluorination of N-protected (2S,4R)-4-hydroxyproline with 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (Fluolead). The 4-fluoropyrrolidine-2-carbonyl fluorides were converted to useful intermediates such as 4-fluoropyrrolidine-2-carboxamides, -N-methoxy-N-methylcarboxamide (Weinreb amide), -carboxylate methyl esters, and -carbonitriles in excellent yields. The crystalline N-Fmoc-cis-4- fluoropyrrolidine-2-carbonyl fluoride 2a is a particularly useful synthon due to its high yield of preparation and easy isolation as an enantiomerically pure compound by crystallization. Thus, the methodology using the synthons prepared by the stereospecific double fluorination has enabled a significant decrease in the synthetic steps needed for the preparation of the 4-fluoropyrrolidine derivatives useful for medicinal applications.