403656-65-5

Basic information

• Product Name: (4R)-4-(diphenylmethyl)-3-[(3R)-3-(ethoxycarbonyl)-4-(3'-methoxyphenyl)]butanoyl-2-oxazolidinone
• Synonyms: (4R)-4-(diphenylmethyl)-3-[(3R)-3-(ethoxycarbonyl)-4-(3'-methoxyphenyl)]butanoyl-2-oxazolidinone
• CAS NO: 403656-65-5
• Molecular Weight: 501.579
• Mol File: 403656-65-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (4R)-4-(diphenylmethyl)-3-[(3R)-3-(ethoxycarbonyl)-4-(3'-methoxyphenyl)]butanoyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-4-(diphenylmethyl)-3-[(3R)-3-(ethoxycarbonyl)-4-(3'-methoxyphenyl)]butanoyl-2-oxazolidinone(403656-65-5)
• EPA Substance Registry System: (4R)-4-(diphenylmethyl)-3-[(3R)-3-(ethoxycarbonyl)-4-(3'-methoxyphenyl)]butanoyl-2-oxazolidinone(403656-65-5)

Safety Data

• Hazardous Substances Data: 403656-65-5(Hazardous Substances Data)

Upstream product

• 97-94-9 triethyl borane 
• 874-98-6 1-bromomethyl-3-methoxybenzene 
• 187929-04-0 (E)-(4R)-3-(3-ethoxycarbonyl-2-propenoyl)-4-diphenyl-methyl-2-oxazolidinone 

Downstream Products

• 403656-70-2 (2R,3R)-2,3-bis-(3'-methoxybenzyl)succininc acid 4-ethyl ester 
• 80704-91-2 (3R,4R)-3,4-bis<(3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 403656-69-9 (R)-4-(diphenylmethyl)-3-[(2R,3R)-2-(3'-methoxyphenyl)methyl-3-(ethoxycarbonyl)-4-(3'-methoxyphenyl)]butanoyl-2-oxazolidinone 

Relevant articles and documents

Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-Enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid

Lewis acid-mediated conjugate addition of alkyl radicals to a differentially protected fumarate 10 produced the monoalkylated succinates with high chemical efficiency and excellent stereoselectivity. A subsequent alkylation or an aldol reaction furnished the disubstituted succinates with syn configuration. The chiral auxiliary, 4-diphenylmethyl-2-oxazolidinone, controlled the stereoselectivity in both steps. Manipulation of the disubstituted succinates obtained by alkylation furnished the natural products (-)-enterolactone, (-)-arctigenin, and (-)-isoarctigenin. The overall yields for the target natural products were 20-26% over six steps. Selective functionalization of the disubstituted succinates obtained by aldol condensation gave the paraconic acid natural products (-)-nephrosteranic acid (8) and (-)-roccellaric acid (9). The overall yield of the natural products 8 and 9 over four steps was 53% and 42%, respectively.