374072-07-8

Basic information

• Product Name: Acetamide, 2,2,2-trifluoro-N-[2-(4-hydroxyphenyl)ethyl]-N-[[4-methoxy-3,5-bis(phenyl methoxy)phenyl]methyl]-
• CAS NO: 374072-07-8
• Molecular Formula: C32H30F3NO5
• Molecular Weight: 565.589
• Mol File: 374072-07-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Acetamide, 2,2,2-trifluoro-N-[2-(4-hydroxyphenyl)ethyl]-N-[[4-methoxy-3,5-bis(phenyl methoxy)phenyl]methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetamide, 2,2,2-trifluoro-N-[2-(4-hydroxyphenyl)ethyl]-N-[[4-methoxy-3,5-bis(phenyl methoxy)phenyl]methyl]-(374072-07-8)
• EPA Substance Registry System: Acetamide, 2,2,2-trifluoro-N-[2-(4-hydroxyphenyl)ethyl]-N-[[4-methoxy-3,5-bis(phenyl methoxy)phenyl]methyl]-(374072-07-8)

Safety Data

• Hazardous Substances Data: 374072-07-8(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 13326-69-7 methyl 3,5-bis(benzyloxy)-4-methoxybenzoate 
• 24093-81-0 methyl 3,5-dihydroxy-4-methoxybenzoate 
• 13326-72-2 3,5-bis(benzyloxy)-4-methoxybenzaldehyde 
• 99-24-1 methyl galloate 
• 27229-56-7 [3,5-bis(benzyloxy)-4-methoxyphenyl]methanol 
• 412009-82-6 N-(3,5-dibenzyloxy-4-methoxy)benzyl-N-(4-hydroxyphenyl)ethylamine 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 374072-15-8 6,8-dibenzyloxy-7-methoxy-2-trifluoroacetyl-2,3,4,5-tetrahydro-1H-[2]benzazepine-5-spiro-1'-cyclohexa-2',5'-diene-4'-one 

Relevant articles and documents

Biomimetic synthesis of (±)-galanthamine and asymmetric synthesis of (-)-galanthamine using remote asymmetric induction

(±)-Galanthamine (1) was synthesized in excellent yield by applying PIFA-mediated oxidative phenol coupling of N-(4-hydroxy)phenethyl-N-(3′, 4′,5′-trialkoxy)benzyl formamide (15b) as a key step. Because of the symmetrical characteristics of the pyrogallol moiety in the substrate (15b), the phenol coupling resulted in a sole coupling product except for volatile components from the oxidizing agent. On the basis of the successful results of the above strategy, (-)-galanthamine (1) was synthesized by employing a novel remote asymmetric induction, where conformation of the seven-membered ring in the product of the phenol coupling was restricted by forming a fused-chiral imidazolidinone ring with D-phenylalanine on the benzylic C-N bond of the tri-O-alkylated gallyl amino moiety. The conformational restriction and successive debenzylation of the protected hydroxyl groups on the pyrogallol ring caused diastereoselective cyclization to yield a cyclic ether having the desired stereochemistry for the synthesis of (-)-1.