117833-93-9

Basic information

• Product Name: (Z)-(R)-N-Cbz-2,2-dimethyl-4-(4-cyano-1-butenyl)oxazolidine
• CAS NO: 117833-93-9
• Molecular Weight: 314.384
• Mol File: 117833-93-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (Z)-(R)-N-Cbz-2,2-dimethyl-4-(4-cyano-1-butenyl)oxazolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-(R)-N-Cbz-2,2-dimethyl-4-(4-cyano-1-butenyl)oxazolidine(117833-93-9)
• EPA Substance Registry System: (Z)-(R)-N-Cbz-2,2-dimethyl-4-(4-cyano-1-butenyl)oxazolidine(117833-93-9)

Safety Data

• Hazardous Substances Data: 117833-93-9(Hazardous Substances Data)

Upstream product

• 117833-92-8 (4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde 
• 117834-00-1 4-(triphenylphosphoranylidene)butanenitrile 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 

Downstream Products

• 117833-95-1 (R)-4-((Z)-5-tert-Butoxycarbonylamino-pent-1-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 
• 117833-97-3 (Z)-(R)-2-<<(benzyloxy)carbonyl>amino>-7-<<(tert-butyloxy)carbonyl>amino>-3-heptenoic acid 
• 133626-15-0 ((Z)-(R)-6-tert-Butoxycarbonylamino-1-hydroxymethyl-hex-2-enyl)-carbamic acid benzyl ester 
• 117833-90-6 (S)-2-amino-7-(Boc-amino)heptanoic acid 

Relevant articles and documents

Synthesis of Chiral Vinylglycines

(R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8.Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (>95percent ee) and double-bond geometry.D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives β,γ-unsaturated amino acids with the L configuration.The double-bond geometry is controlled by the nature of the phosphorous ylide employed.The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.