1380521-86-7

Basic information

• Product Name: tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate
• Synonyms: tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate
• CAS NO: 1380521-86-7
• Molecular Weight: 513.6
• Mol File: 1380521-86-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate(1380521-86-7)
• EPA Substance Registry System: tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate(1380521-86-7)

Safety Data

• Hazardous Substances Data: 1380521-86-7(Hazardous Substances Data)

Upstream product

• 27784-76-5 tert-butyl diethylphosphonoacetate 
• 1380521-84-5 tert-butyl (E)-4-(2',4',5'-trifluorophenyl)but-2-enoate 
• 14429-03-9 (R)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine 

Downstream Products

• 654671-78-0 sitagliptin phosphate 
• 1393363-87-5 (R)-N-benzyl-1-(2',4',5'-trifluorophenyl)-4-oxo-4-{3''-(trifluoromethyl)-5'',6''-dihydro-1'',2'',4''-triazolo[4,3-α]pyrazin-7''(8''H)-yl}butan-2-amine 
• 486460-32-6 sitagliptin 

Relevant articles and documents

Asymmetric synthesis of (-)-(R)-sitagliptin

The asymmetric synthesis of (-)-(R)-sitagliptin was achieved in seven steps from commercially available starting materials using the highly diastereoselective conjugate additions of either lithium (R)-N-benzyl-N- (α-methylbenzyl)amide or lithium (R)-N-benzyl-N-(α-methyl-p- methoxybenzyl)amide to tert-butyl 4-(2′,4′,5′-trifluorophenyl) but-2-enoate to install the correct stereochemistry. Subsequent sequential acid-catalysed hydrolysis of the resultant β-amino esters, HOBt/EDC mediated coupling with the triazolopyrazine fragment, and hydrogenolysis gave (-)-(R)-sitagliptin in 43% and 42% overall yields, respectively.