72155-51-2

Usage

InChI:InChI=1/C11H15NO3/c12-9(10(13)7-11(14)15)6-8-4-2-1-3-5-8/h1-5,9-10,13H,6-7,12H2,(H,14,15)/t9-,10+/m0/s1

Upstream product

• 72155-49-8 N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid 
• 63-91-2 L-phenylalanine 
• 95437-43-7 (S)-2-(N,N-dibenzylamino)-3-phenylpropanoic acid 
• 188774-99-4 tert-butyl 4-(N,N-dibenzylamino)-3-oxo-5-phenylpentanoate 
• 72155-47-6 N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid ethyl ester 
• 390377-29-4 tert-butyl (3R,4S)-4-(N,N-dibenzylamino)-3-hydroxy-5-phenylpentanoate 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 390377-68-1 (3R,4S)-4-(N,N-dibenzylamino)-3-hydroxy-5-phenylpentanoic acid 

Downstream Products

• 72155-55-6 2-oxazolidinone of 4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid 

Relevant academic research and scientific papers

A silver-promoted solid-phase guanidylation process enables the first total synthesis of stictamide A

The first total synthesis of stictamide A, a structurally unique peptide with a statine motif and a N-prenyl modified arginine in the side chain, is disclosed. The requisite statine was achieved via stereoselective hydrogenation of a functionalized ketone. The N-prenyl modified arginine was constructed by a novel silver-promoted solid-phase strategy for the first time. This synthetic method can be generally applied to the efficient synthesis of peptides containing statine and/or arginine N-alkylation groups.

Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes

N,N-Dibenzylamino aldehydes 1 react with Reformatsky's reagent leading to anti-γ-dibenzylamino-β-hydroxy esters 2 as the major stereoisomers. Treatment of 2 with TFA followed by hydrogenolysis on Pearlman's catalyst yields the corresponding γ-amino-β-hydroxy acids 10. Contrarily, some N-butoxycarbonyl (Boc) amino aldehydes lead to syn-γ-tert-butoxycarbonylamino-β-hydroxy esters as the major product.

Synthesis of analogues of the carboxyl protease inhibitor pepstatin. Effect of structure on inhibition of pepsin and renin

Analogues of the carboxyl protease inhibitor, pepstatin, were synthesized from optically pure forms of N-(tert-butoxycarbonyl)-4-amino-3-hydroxy-6-methylheptanoic acid (Boc-Sta), and the inhibition of pepsin and renin was determined. In addition, the new