1393834-15-5

Basic information

• Product Name: (4R,Z)-N-(4'-benzyloxy-but-3'-enoyl)-4,5,5-triphenyloxazolidin-2-one
• Synonyms: (4R,Z)-N-(4'-benzyloxy-but-3'-enoyl)-4,5,5-triphenyloxazolidin-2-one
• CAS NO: 1393834-15-5
• Molecular Weight: 489.571
• Mol File: 1393834-15-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (4R,Z)-N-(4'-benzyloxy-but-3'-enoyl)-4,5,5-triphenyloxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,Z)-N-(4'-benzyloxy-but-3'-enoyl)-4,5,5-triphenyloxazolidin-2-one(1393834-15-5)
• EPA Substance Registry System: (4R,Z)-N-(4'-benzyloxy-but-3'-enoyl)-4,5,5-triphenyloxazolidin-2-one(1393834-15-5)

Safety Data

• Hazardous Substances Data: 1393834-15-5(Hazardous Substances Data)

Upstream product

• 73710-76-6 C₁₃H₁₆O₃ 
• 100-51-6 benzyl alcohol 
• 156481-74-2 (R)-4-phenyl-5,5-diphenyl-oxazolidin-2-one 
• 162551-89-5 4-(phenylmethoxy)-2-butenoic acid 
• 70150-60-6 ethyl 2E-4-(benzyloxy)-2-butenoate 

Relevant articles and documents

Syn-effect' in the diastereoselective alkylation of 3-[(E)-α,β-unsaturated-γ-substituted]-N-acyloxazolidinones

Synthetic methods for the formation of alkenes usually produce the E-alkene because it is more stable. However, in isomerization reaction (double bond migration) that takes place in α, β-unsaturated carbonyl compounds, when these carbonyl compounds are exposed to strong bases, furnish Z-alkenes highly stereoselective depending on the γ-substituent in the α, β-unsaturated carbonyl. This stereoselectivity can be attributed to the known Syn-effect. The synthetic value of this methodology is the achievement of chiral alcohol bearing an electron rich Z-alkene, as well as substituted, which was accomplished via removal of the oxazolidinone moiety under treatment with NaBH4, THF-H2O.