72155-49-8

Upstream product

• 72155-47-6 N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid ethyl ester 
• 100-39-0 benzyl bromide 
• 229981-33-3 tert-butyl (2S,3R)-2-benzyl-3--5-oxo-1-pyrrolidinecarboxylate 
• 101669-81-2 (3R,4S)-4-<(tert-butoxycarbonyl)amino>-3-hydroxy-5-phenylpentanoic acid methyl ester 
• 864165-75-3 methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonylamino)-2-phenylethyl]-oxirane-2-carboxylate 
• 864165-73-1 C₁₈H₂₃NO₆ 
• 864165-71-9 methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonyl-N-hydroxymethylamino)-2-phenylethyl]-oxirane-2-carboxylate 
• 321164-87-8 (S)-4-(tert-butoxycarbonylamino)-5-phenyl-1-trimethylsilylpent-1-yn-3-one 
• 87694-53-9 Boc-Phe-OH N,O-dimethyl hydroxamate 

Downstream Products

• 72155-51-2 (3R,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid 
• 178113-66-1 (3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid 
• 159542-04-8 (-)-hapalosin 
• 72155-55-6 2-oxazolidinone of 4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid 

Relevant academic research and scientific papers

An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (?)-hapalosin

A diastereoselective approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones 1 (P1 = TBS, P2 = H) has been developed through a stereoselective tandem Barbier process of (R,SRS)-8 with alkyl and aryl bromide. The stereochemistry at the C-5 stereogenic center of the trans-4-hydroxy-5-substituted 2-pyrrolidinones was solely controlled by α-alkoxy substitution. This effective approach was successfully used to prepare a variety of substituted (3R,4S)-statines 2. In addition, two bioactive natural products of (+)-preussin 4 and hapalosin 5 were effectively synthesized through this stereoselective tandem Barbier process.

Stereodivergent approach to both syn- and anti-isomers of γ-amino-β-hydroxy acids: (3S,4S)- and (3R,4S)-AHPPA derivatives

A stereodivergent approach employing an N-hydroxymethyl group has been utilized to produce both diastereomeric derivatives of (3S,4S)-AHPPA 3 and (3R,4S)-AHPPA 4, via an intramolecular conjugate addition and an intramolecular epoxidation, respectively. Th

A synthetic approach to 3-hydroxy 4-substituted carboxylic acids based on the stereoselective reduction of 1-trimethylsilyl-1-alkyn-3-ones

The oxazaborolidine-mediated reduction of chiral, 4-substituted 1-trimethylsilyl-1-alkyn-3-ones followed by hydroboration affords syn or anti 3-hydroxy 4-substituted carboxylic acids, common substructures of a number of biologically active macrolides, peptides and depsipeptides, with high control on the new C(3) stereocenter. This strategy has been applied to the synthesis of (3S,4S)-3-hydroxy-4-methylheptanoic acid and of N-Boc-statine, constituents of permentin A and pepstatin, respectively. (C) 2000 Elsevier Science Ltd.

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