52186-44-4

Basic information

• Product Name: (S)-N-benzyloxycarbonyl-4-hydroxy-3-hydroxymethylphenylalanine
• Synonyms: (S)-N-benzyloxycarbonyl-4-hydroxy-3-hydroxymethylphenylalanine
• CAS NO: 52186-44-4
• Molecular Weight: 345.352
• Mol File: 52186-44-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-N-benzyloxycarbonyl-4-hydroxy-3-hydroxymethylphenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-benzyloxycarbonyl-4-hydroxy-3-hydroxymethylphenylalanine(52186-44-4)
• EPA Substance Registry System: (S)-N-benzyloxycarbonyl-4-hydroxy-3-hydroxymethylphenylalanine(52186-44-4)

Safety Data

• Hazardous Substances Data: 52186-44-4(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 1164-16-5 Z-L-Tyr-OH 
• 698386-61-7 benzyl (S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolane-3-carboxylate 
• 698386-62-8 (S)-2-(Benzyloxycarbonyl-hydroxymethyl-amino)-3-(4-hydroxy-3-hydroxymethyl-phenyl)-propionic acid 

Downstream Products

• 1219720-74-7 N-Cbz-3-methyl-L-tyrosine 
• 1219720-76-9 C₂₁H₂₅NO₆ 
• 1219720-75-8 N-Cbz-3-hydroxymethyl-4-methoxy-L-phenylalanine methyl ester 
• 206445-95-6 (S)-3-(5-Acetoxymethyl-2'-chloro-6-trifluoromethanesulfonyloxy-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester 
• 206445-96-7 (S)-3-(5-Acetoxymethyl-6-trifluoromethanesulfonyloxy-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester 
• 206445-93-4 (S)-3-(5-Acetoxymethyl-2'-chloro-6-hydroxy-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester 
• 206445-97-8 (S)-3-(5-Acetoxymethyl-2'-chloro-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester 
• 206445-94-5 (S)-3-(5-Acetoxymethyl-6-hydroxy-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester 
• 206445-98-9 (S)-3-(5-Acetoxymethyl-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester 
• 206445-99-0 (S)-2-Benzyloxycarbonylamino-3-(5-bromomethyl-2'-chloro-biphenyl-3-yl)-propionic acid methyl ester 
• 206445-92-3 (S)-2-Benzyloxycarbonylamino-3-(8-bromo-2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)-propionic acid methyl ester 
• 206446-00-6 (S)-2-Benzyloxycarbonylamino-3-(5-bromomethyl-biphenyl-3-yl)-propionic acid methyl ester 
• 206445-91-2 N-(benzyloxycarbonyl)-3-bromo-5-(hydroxymethyl)-(S)-tyrosine methyl ester 

Relevant articles and documents

A new approach to the synthesis of l-3-hydroxy-4-methoxy-5-methyl-phenylalanine derivatives from l-tyrosine

A practical procedure to regioselectively install a methyl group and a phenolic hydroxyl group onto l-tyrosine was developed. By using this approach, protected l-3-hydroxy-4-methoxy-5-methyl-phenylalanine and l-3-hydroxy-4-methoxy-5-methyl-phenylalanol, which are utilized in efficient syntheses of the relevant tetrahydroisoquinoline alkaloids, were prepared conveniently with high yield.

A convenient two step transformation of tyrosine into the antihypertensive amino acid (S)-4-hydroxy-3-hydroxymethylphenylalanine

Treatment of tyrosine with paraformaldehyde and catalytic amounts of p-toluenesulfonic acid, at reflux in toluene, directly generates benzyl (S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolane-3-carboxylate, which on treatment with boron trichloride in dichloromethane, affords (S)-4-hydroxy-3-hydroxymethylphenylalanine.