86099-14-1

Basic information

• Product Name: L-Tyrosine, N-methyl-N-[(phenylmethoxy)carbonyl]-
• CAS NO: 86099-14-1
• Molecular Formula: C18H19NO5
• Molecular Weight: 329.353
• Mol File: 86099-14-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: L-Tyrosine, N-methyl-N-[(phenylmethoxy)carbonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Tyrosine, N-methyl-N-[(phenylmethoxy)carbonyl]-(86099-14-1)
• EPA Substance Registry System: L-Tyrosine, N-methyl-N-[(phenylmethoxy)carbonyl]-(86099-14-1)

Safety Data

• Hazardous Substances Data: 86099-14-1(Hazardous Substances Data)

Upstream product

• 537-49-5 N-methyl-L-tyrosine 
• 501-53-1 benzyl chloroformate 
• 1164-16-5 Z-L-Tyr-OH 
• 86827-18-1 N-benzyloxycarbonyl-O-benzyl-L-tyrosine 
• 225386-51-6 phenylmethyl (4S)-5-oxo-4-({4-[(phenylmethyl)oxy]phenyl}methyl)-1,3-oxazolidine-3-carboxylate 
• 205866-50-8 (S)-3-benzyloxycarbonyl-4-(4-hydroxyphenyl)methyloxazolidin-5-one 

Downstream Products

• 86099-15-2 ((S)-2,8-Dioxo-1-oxa-spiro[4.5]deca-6,9-dien-3-yl)-methyl-carbamic acid benzyl ester 
• 108969-88-6 N-benzyloxycarbonyl-2,6-dichloro-N-methyltyrosine 
• 108969-86-4 N-benzyloxycarbonyl-2,6-dibromo-N-methyltyrosine 
• 675129-49-4 Cbz-N-methyl-Tyr-Gly-OMe 
• 91474-98-5 methyl O,N-dimethyl-L-tyr-L-alaninate 
• 69340-16-5 methyl L-ala-O,N-dimethyl-L-tyr-L-alaninate 
• 91475-00-2 methyl N-boc-L-ala-O,N-dimethyl-L-tyr-L-alaninate 
• 115441-65-1 methyl N-Cbz-N,O-dimethyl-L-tyrosyl-L-alaninate 
• 675129-50-7 Cbz-N,O-dimethyl-Tyr-Gly-OMe 
• 675129-46-1 Boc-Gly-N,O-dimethyl-Tyr-Ala-OMe 
• 675129-51-8 Boc-Ala-N,O-dimethyl-Tyr-Gly-OMe 
• 675129-52-9 Boc-D-Ala-Ala-N,O-dimethyl-Tyr-Gly-OMe 
• 675129-44-9 Boc-Gly-Ala-N,O-dimethyl-Tyr-Ala-OMe 
• 675129-47-2 Boc-D-Ala-Gly-N,O-dimethyl-Tyr-Ala-OMe 

Relevant articles and documents

Effective methods for the synthesis of N-methyl β-amino acids from all twenty common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones

N-Methyl β-amino acids are generally required for application in the synthesis of potentially bioactive modified peptides and other oligomers. Previous work highlighted the reductive cleavage of 1,3-oxazolidin-5-ones to synthesise N-methyl α-amino acids. Starting from α-amino acids, two approaches were used to prepare the corresponding N-methyl β-amino acids. First, α-amino acids were converted to N-methyl α-amino acids by the so-called '1,3-oxazolidin-5-one strategy', and these were then homologated by the Arndt-Eistert procedure to afford N-protected N-methyl β-amino acids derived from the 20 common α-amino acids. These compounds were prepared in yields of 23-57% (relative to N-methyl α-amino acid). In a second approach, twelve N-protected α-amino acids could be directly homologated by the Arndt-Eistert procedure, and the resulting β-amino acids were converted to the 1,3-oxazinan-6-ones in 30-45% yield. Finally, reductive cleavage afforded the desired N-methyl β-amino acids in 41-63% yield. One sterically congested β-amino acid, 3-methyl-3-aminobutanoic acid, did give a high yield (95%) of the 1,3-oxazinan-6-one (65), and subsequent reductive cleavage gave the corresponding AIBN-derived N-methyl β-amino acid 61 in 71% yield (Scheme 2). Thus, our protocols allow the ready preparation of all N-methyl β-amino acids derived from the 20 proteinogenic α-amino acids.

Regioselective synthesis of 14-membered biaryl ethers: Total synthesis of RA-VII and deoxybouvardin

In order to obtain a key compound (22a'') for synthesis of RA-VII (1) and deoxybouvardin (2), construction of the 14-membered ring system was performed by means of thallium trinitrate-mediated oxidation of the tetrahalogeno amides 5-7. The dibromo dichlor