130608-06-9

Upstream product

• 13673-95-5 (S)-methyl 2-hydroxy-3-phenylpropanoate 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 

Downstream Products

• 130608-09-2 (R)-2-(N'-tert-Butoxycarbonyl-hydrazino)-3-phenyl-propionic acid methyl ester 
• 150447-60-2 H-(N²-Boc)aPhe-OMe 
• 14381-08-9 (R)-2-(N'-tert-Butoxycarbonyl-hydrazino)-3-phenyl-propionic acid 
• 40248-79-1 (R)-2-Hydrazino-3-phenyl-propionic acid methyl ester 
• 124790-74-5 (R)-2-azido-3-phenylpropionic acid methyl ester 
• 116911-32-1 (S)-2-azido-3-phenylpropionic acid methyl ester 

Relevant academic research and scientific papers

THE PREPARATION OF 2-HYDRAZINYL ESTERS IN HIGH OPTICAL PURITY FROM 2-SULFONYLOXY ESTERS

Chiral 2-triflyloxy esters, prepared from chiral 2-hydroxy esters, react enantiospecifically with BocNHNH2 to produce optically pure 2-hydrazinyl ester derivatives in high yields.The reaction of 2-nosyloxy esters with BocNHNH2 gives 2-(Boc-hydrazinyl) esters, thus providing an efficient (albeit slow) method for the conversion of esters to 2-hydrazinyl ester derivatives.

Preparation of (R)-2-azidoesters from 2-((p-nitrobenzene)sulfonyl)oxy esters and their use as protected amino acid equivalents for the synthesis of di- and tripeptides containing D-amino acid constituents

(R)-2-Azidoesters and their derived (R)-2-azido acids are readily prepared from common amino acids by an inversion methodology that employs (S)-2-nosyloxyesters as key intermediates. The (R)-2-azidoesters can be used as protected amino acid equivalents in peptide synthesis. Basic hydrolysis frees the carboxyl group. Triphenylphosphine/water is used to free the amine group. By these reactions a variety of L-D and D-L dipeptides, L-D-L tripeptides, and depsipeptides can be prepared easily in good yields, and without detectable epimerization.