1185729-94-5

Basic information

• Product Name: (+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate
• Synonyms: (+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate
• CAS NO: 1185729-94-5
• Molecular Weight: 435.48
• Mol File: 1185729-94-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate(1185729-94-5)
• EPA Substance Registry System: (+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate(1185729-94-5)

Safety Data

• Hazardous Substances Data: 1185729-94-5(Hazardous Substances Data)

Upstream product

• 1185729-93-4 (2S,5R,6S)-5-hydroxy-6-[2-(4-oxo-4H-quinazolin-3-ylmethyl)-allyl]piperdine-1-carboxylic acid benzyl ester 
• 866488-35-9 (E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate 
• 491-36-1 4-Hydroxyquinazoline 
• 1203455-33-7 (2S,3R)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester 

Downstream Products

• 27257-66-5 febrifugine dihydrochloride 

Relevant articles and documents

An asymmetric synthesis of febrifugine, halofuginone and their hemiketal isomers

A new synthesis of both enantiomers of naturally occurring febrifugine (1) and its analogue halofuginone (3) are reported. This robust route relies on an enzymatic kinetic resolution (EKR)-cross metathesis (CM) sequence, performed on allylic alcohol 8. A diastereoselective Lewis acid-mediated cyclisation of resultant enone 6 affords piperidine 12. In relation to its enantiomeric excess, values of 87 and 88% e.e were obtained for both enantiomers of 12 and for (?)-12 this was increased to 98% e.e by conducting the resolution process twice. A bromination (featuring an in situ temporary alcohol protection), alkylation and amino-deprotection sequence finally afforded the target compounds (+)- and (?)-1, and (+)- and (?)-3. Studies demonstrate that, as their ammonium salts, the compounds are stereochemically stable. However, as their free-bases, particularly in chloroform, C-2 isomerisation occurs. This isomerisation has been taken advantage of synthetically to provide enantioenriched (+)-isofebrifugine (2) and both enantiomers of isohalofuginone (14).