722499-72-1

Basic information

• Product Name: 4-Imidazolidinone, 3-[2-(4-hydroxyphenyl)ethyl]-2-[4-methoxy-3,5-bis(phenylmethoxy)phenyl ]-5-(phenylmethyl)-1-(trifluoroacetyl)-, (2R,5R)-
• CAS NO: 722499-72-1
• Molecular Formula: C41H37F3N2O6
• Molecular Weight: 710.75
• Mol File: 722499-72-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-Imidazolidinone, 3-[2-(4-hydroxyphenyl)ethyl]-2-[4-methoxy-3,5-bis(phenylmethoxy)phenyl ]-5-(phenylmethyl)-1-(trifluoroacetyl)-, (2R,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Imidazolidinone, 3-[2-(4-hydroxyphenyl)ethyl]-2-[4-methoxy-3,5-bis(phenylmethoxy)phenyl ]-5-(phenylmethyl)-1-(trifluoroacetyl)-, (2R,5R)-(722499-72-1)
• EPA Substance Registry System: 4-Imidazolidinone, 3-[2-(4-hydroxyphenyl)ethyl]-2-[4-methoxy-3,5-bis(phenylmethoxy)phenyl ]-5-(phenylmethyl)-1-(trifluoroacetyl)-, (2R,5R)-(722499-72-1)

Safety Data

• Hazardous Substances Data: 722499-72-1(Hazardous Substances Data)

Upstream product

• 18942-49-9 Boc-D-Phe-OH 
• 51-67-2 tyrosamine 
• 722499-78-7 2-(R)-tert-butoxycarbonylamino-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropionamide 
• 722499-70-9 2-(R)-amino-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropionamide 
• 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 
• 27229-56-7 [3,5-bis(benzyloxy)-4-methoxyphenyl]methanol 
• 407-25-0 trifluoroacetic anhydride 
• 722499-71-0 (2S,5R)-5-benzyl-2-(3,5-dibenzyloxy-4-methoxyphenyl)-3-[2-(4-hydroxyphenyl)ethyl]imidazolidin-4-one 

Downstream Products

• 929211-74-5 C₂₅H₂₆N₂O₅ 
• 41303-74-6 N-desmethyl galantamine 
• 357-70-0 Galantamine 
• 722499-81-2 C₂₇H₂₅F₃N₂O₅ 
• 722499-75-4 C₂₇H₂₃F₃N₂O₅ 
• 722499-82-3 C₂₇H₂₅F₃N₂O₆ 
• 722499-74-3 C₂₇H₂₃F₃N₂O₆ 
• 722499-80-1 C₂₈H₂₂F₆N₂O₈S 
• 722499-73-2 C₄₁H₃₅F₃N₂O₆ 

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.