860781-14-2

Upstream product

• 860781-11-9 tert-butyl (2S,3S,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-hydroxyprolinate 
• 91237-84-2 N-BOC-proline tert-butyl ester 
• 166410-05-5 tert-butyl N^α-Boc-4-keto-L-prolinate 
• 860781-19-7 tert-butyl (2S)-[3,3-²H₂]-N-tert-butoxycarbonyl-4-oxoprolinate 
• 860781-20-0 tert-butyl (2S,3S)-[3-²H₁]-N-tert-butoxycarbonyl-4-oxoprolinate 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

HETEROARYL COMPOUNDS FOR TREATMENT OF COMPLEMENT FACTOR D MEDIATED DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement factor D or a pharmaceutically acceptable salt or composition thereof are provided. The inhibitors described herein target factor D and inhibit or regulate the complement cascade. The inhibitors of factor D described herein reduce the excessive activation of complement.

Two separate and distinct syntheses of stereospecifically deuteriated samples of (2S)-proline

Two distinct syntheses of samples of the amino acid l-proline which are stereospecifically deuteriated on the β-carbon atom are reported. In the first of these, the labelled diazoketones 6, prepared by a chemico-enzymatic synthesis, have been photolysed in alkaline conditions to give the corresponding labelled methyl pyroglutamates 10 via hydrolysis and intramolecular trapping of the resultant ketene intermediates 9. These were then converted into (2S,3S)-[3-2H1]- and (2S,3R)-[2,3-2H 2]-proline, 1a and 1b respectively. The second synthesis provides (2S)-[3,3-2H2]-, (2S,3S)- and (2S,3R)-[3- 2H1]-proline, 1d, 1a and 1c respectively, and has as its key step the highly stereoselective hydrolysis of the silylenol ethers 14 and 14a respectively in which deuteriation or protonation occurs from the re-face of the enol ether. The Royal Society of Chemistry 2006.

Synthesis of (2S,3R)- and (2S,3S)-[3-2H1]-proline via highly stereoselective hydrolysis of a silyl enol ether

A straightforward synthesis of (2S)-[3,3-2H2]-proline 1c and (2S,3R)- and (2S,3S)-[3-2H1]-proline, 1b and 1a, respectively, has been devised. The key step of the route to the latter compounds involves highly stereoselective hydrolysis of the silyl enol ethers 3 and 3a, respectively, with protonation (deuteriation) from the re-face of the silyl enol ether.