860781-13-1

Basic information

• Product Name: tert-butyl (2S,3R,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate
• Synonyms: tert-butyl (2S,3R,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate
• CAS NO: 860781-13-1
• Molecular Weight: 442.538
• Mol File: 860781-13-1.mol

Chemical Properties

• CAS DataBase Reference: tert-butyl (2S,3R,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (2S,3R,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate(860781-13-1)
• EPA Substance Registry System: tert-butyl (2S,3R,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate(860781-13-1)

Safety Data

• Hazardous Substances Data: 860781-13-1(Hazardous Substances Data)

Upstream product

• 166410-25-9 tert-butyl (2S)-N-tert-butoxycarbonyl-3,4-dehydro-4-trimethylsilyloxyprolinate 
• 166410-05-5 tert-butyl N^α-Boc-4-keto-L-prolinate 
• 860781-21-1 tert-butyl (2S,3R)-[3-²H₁]-N-tert-butoxycarbonyl-4-oxoprolinate 
• 860781-10-8 tert-butyl (2S,3R,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-hydroxyprolinate 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant articles and documents

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.

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.