260997-24-8

Basic information

• Product Name: (3R,5E,αR)-isopropyl 3-(N-benzyloxycarbonyl-N-α-methylbenzylamino)hept-5-enoate
• Synonyms: (3R,5E,αR)-isopropyl 3-(N-benzyloxycarbonyl-N-α-methylbenzylamino)hept-5-enoate
• CAS NO: 260997-24-8
• Molecular Weight: 423.552
• Mol File: 260997-24-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (3R,5E,αR)-isopropyl 3-(N-benzyloxycarbonyl-N-α-methylbenzylamino)hept-5-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,5E,αR)-isopropyl 3-(N-benzyloxycarbonyl-N-α-methylbenzylamino)hept-5-enoate(260997-24-8)
• EPA Substance Registry System: (3R,5E,αR)-isopropyl 3-(N-benzyloxycarbonyl-N-α-methylbenzylamino)hept-5-enoate(260997-24-8)

Safety Data

• Hazardous Substances Data: 260997-24-8(Hazardous Substances Data)

Upstream product

• 260997-21-5 isopropyl (2E,5E)-hepta-2,5-dienoate 
• 124-38-9 carbon dioxide 
• 501-53-1 benzyl chloroformate 
• 100-51-6 benzyl alcohol 
• 31139-36-3 dibenzyl dicarbonate 
• 260997-31-7 (E)-(R)-3-((R)-1-Phenyl-ethylamino)-hept-5-enoic acid isopropyl ester 

Downstream Products

• 260997-29-3 (4R,6R,1'R,αR)-3-(α-methylbenzyl)-4-(isopropoxycarbonylmethyl)-6-(1'-aminoethyl)-1,3-oxazin-2-one 
• 260997-26-0 (4R,6R,1'S,αR)-3-(α-methylbenzyl)-4-(isopropoxycarbonylmethyl)-6-(1'-iodoethyl)-1,3-oxazin-2-one 

Relevant articles and documents

Asymmetric total synthesis of sperabillins B and D via lithium amide conjugate addition

Diastereoselective conjugate addition of homochiral lithium (R)-N-allyl-N-α-methylbenzylamide to methyl (2E,5E)-hepatadienoate, followed by protecting group manipulation and subsequent iodocyclocarbamation allows a concise route to the core fragment, methyl (3R,5R,6R)-3,6-diamino-5- hydroxyheptanoate, of sperabillins B and D. Differentiation between the C-3 and C-6 primary amino groups of this core amino acid was readily achieved by treatment with acetone, giving the 5,6-isopropylidene and C-3-imine protected diamine, with subsequent regioselective acylation of the C-6-nitrogen facilitating the total synthesis of sperabillin D in 10.8% overall yield, and the first asymmetric synthesis of sperabillin B in 5.8% overall yield.