785790-03-6

Basic information

• Product Name: (3R,5E,αR)-methyl 3-(N-tert-butoxycarbonyl-N-α-methylbenzylamino)hept-5-enoate
• CAS NO: 785790-03-6
• Molecular Weight: 361.481
• Mol File: 785790-03-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3R,5E,αR)-methyl 3-(N-tert-butoxycarbonyl-N-α-methylbenzylamino)hept-5-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,5E,αR)-methyl 3-(N-tert-butoxycarbonyl-N-α-methylbenzylamino)hept-5-enoate(785790-03-6)
• EPA Substance Registry System: (3R,5E,αR)-methyl 3-(N-tert-butoxycarbonyl-N-α-methylbenzylamino)hept-5-enoate(785790-03-6)

Safety Data

• Hazardous Substances Data: 785790-03-6(Hazardous Substances Data)

Upstream product

• 126275-19-2 (R)-N-allyl (1-phenylethyl)amine 

Downstream Products

• 785790-12-7 (4R,6R,1'R,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-azidoethyl)-1,3-oxazin-2-one 
• 624739-12-4 (4R,6S,1'R,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-aminoethyl)-1,3-oxazinan-2-one 
• 785790-21-8 (4R,6R,1'R,αR)-3-(N-α-methylbenzyl)-4-(carboxymethyl)-6-(1'-aminoethyl)-1,3-oxazin-2-one 
• 785790-37-6 (3R,5R,6R,αR)-3-(N-α-methylbenzylamino)-5-hydroxy-6-aminoheptanoic acid 
• 624739-02-2 (4R,6R,1'S,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-iodoethyl)-1,3-oxazinan-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.