700816-76-8

Upstream product

• 160648-53-3 O-acetyl-N-phthaloyl-L-tyrosine methyl ester 
• 196092-88-3 (2R)-O-acetyl-3-bromo-N-phthaloyltyrosine methyl ester 
• 160648-59-9 (2S,3R)-O-acetyl-3-hydroxy-N-phthaloyl-tyrosine methyl ester 
• 1080-06-4 L-Tyr-OMe 
• 39739-09-8 methyl (S)-2-(1,3-dioxoisoindolin-2-yl)-3-(4-hydroxyphenyl)propanoate 
• 863871-23-2 (2S,3R)-3-methoxy-N-phthaloyl-tyrosine methyl ester 
• 188446-24-4 (2R,5S,αR)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 864954-50-7 (2R,5S,αR)-5-[4'-benzyloxy-α-methoxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine 
• 865062-13-1 (R)-O-benzyl-β-methoxy-L-tyrosine allyl ester 
• 864954-51-8 (R)-O-benzyl-β-methoxy-L-tyrosine methyl ester 
• 863871-28-7 (2S,3R)-β-methoxytyrosine methyl ester 

Downstream Products

• 316172-74-4 L-threo-β-methoxyaspartate 

Relevant academic research and scientific papers

Concise synthesis of all stereoisomers of β-methoxytyrosine and determination of the absolute configuration of the residue in callipeltin A

(Chemical Equation Presented) All stereoisomers of β-methoxytyrosine (β-OMeTyr), a stereo-undefined component of callipeltin A, were synthesized from L- and D-tyrosine. The stereochemistry of β-OMeTyr in callipeltin A was determined to be 2R,3R by an oxidative procedure and Marfey's analysis.

Complete stereochemistry of neamphamide A and absolute configuration of the β-methoxytyrosine residue in papuamide B

The absolute stereochemistry of the three unresolved structural components in neamphamide A (1) was determined to be (R)-β-methoxy-L-tyrosine, (2R,3A,4S)-4-amino-7-guanidino-2,3-dihydroxy-heptanoic acid, and (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid. Stereochemical assignments were made by chemical degradation of 1, derivatization of the resulting products, and then spectroscopic and chromatographic comparison of the derivatives with synthetically prepared standards. Using the same analytical protocol developed for 1, the β-methoxytyrosine residue in papuamide B (2) was found to be (R)-β-methoxy-D-tyrosine. This represents a rare example of divergent stereochemistry in an unusual amino acid residue that is present in two closely related classes of peptides.