203798-83-8

Basic information

• Product Name: (E)-3-(3,4-Bis-benzyloxy-phenyl)-acrylic acid (S)-2-(3,4-bis-benzyloxy-phenyl)-1-methoxycarbonyl-ethyl ester
• CAS NO: 203798-83-8
• Molecular Weight: 734.846
• Mol File: 203798-83-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-3-(3,4-Bis-benzyloxy-phenyl)-acrylic acid (S)-2-(3,4-bis-benzyloxy-phenyl)-1-methoxycarbonyl-ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-(3,4-Bis-benzyloxy-phenyl)-acrylic acid (S)-2-(3,4-bis-benzyloxy-phenyl)-1-methoxycarbonyl-ethyl ester(203798-83-8)
• EPA Substance Registry System: (E)-3-(3,4-Bis-benzyloxy-phenyl)-acrylic acid (S)-2-(3,4-bis-benzyloxy-phenyl)-1-methoxycarbonyl-ethyl ester(203798-83-8)

Safety Data

• Hazardous Substances Data: 203798-83-8(Hazardous Substances Data)

Upstream product

• 136749-45-6 (+)-(S)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate 
• 100-44-7 benzyl chloride 
• 203571-41-9 3,4-dibenzyloxycinnamoyl chloride 
• 203798-70-3 (S)-3-(3,4-Bis-benzyloxy-phenyl)-2-hydroxy-propionic acid methyl ester 

Downstream Products

• 203798-86-1 methyl rosmarinate 

Relevant articles and documents

Synthesis of enantiomeric (+)- and (-)-rosmarinic acid methylesters

Starting from L-tyrosine (L-1), the phenyl lactic acid ester (-)-4 was prepared by reported procedures. (-)-4 could then be converted to the benzyl ether (-)-5. From (-)-5, the corresponding optical antipode (+)-5 is available via (+)-6 by Mitsunobu reaction. The enantiomeric excess of 5 was determined by NMR spectroscopy from camphanic acid esters (+)- and (-)-8, respectively. The phenyl lactic acid esters (+)- and (-)-5 were acylated by caffeoyl chloride (9) to yield the O-protected enantiomeric rosmarinic acid esters (+)- and (-)-10. Deprotection of 10 by BCl3 afforded the title compounds (+)- and (-)-11 in fair yields.