116565-10-7

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 591721-45-8 methyl 3-azido-2,4-dihydroxy-4-phenyl-(2R,3S,4R)-butanoate 
• 105181-72-4 (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid 
• 74-88-4 methyl iodide 
• 139163-87-4 (2R,3S)-methyl 3-amino-2-hydroxy-4-phenylbutanoate 
• 67-56-1 methanol 
• 72155-45-4 Boc-L-phenylalaninal 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 186393-18-0 ((S)-1-benzyl-2-cyano-2-hydroxy-ethyl)-carbamic acid tert-butyl ester 
• 209173-80-8 2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 203806-58-0 Acetic acid [(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-triisopropylsilanyloxy-azetidin-2-yl]-phenyl-methyl ester 
• 203806-57-9 (2S,3R)-2-Benzyl-4-oxo-3-triisopropylsilanyloxy-azetidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 105181-72-4 (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid 
• 336611-71-3 [(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 573968-50-0 {(S)-1-[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-ylcarbamoyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester 
• 454423-73-5 (2R,3S)-3-{(S)-2-[(S)-2-Acetylamino-3-(1-trityl-1H-imidazol-4-yl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-N-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-yl)-4-phenyl-butyramide 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 
• 233662-06-1 N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methane sulfonyloxybutane 
• 1234915-47-9 C₂₇H₄₁N₉O₇ 
• 1234915-51-5 C₃₂H₄₅N₅O₉ 

Relevant academic research and scientific papers

Synthesis of macrocyclic α-ketoamide as a selective and reversible immunoproteasome inhibitor

In recent years, the human immunoproteasome has emerged as an attractive therapeutic target for various diseases, leading to a growing interest in the discovery of immunoproteasome inhibitors that selectively target specific subunits. Herein we report the design, synthesis, and evaluation of a new immunoproteasome inhibitor that feature a macrocyclic ring containing an internal α-ketoamide warhead. This compound is a selective and reversible inhibitor of immunoproteasome subunits β1i and β5i and shows essentially no inhibition of constitutive proteasome subunits. [Figure not available: see fulltext.]

Application of the asymmetric aminohydroxylation reaction for the syntheses of HIV-protease inhibitor, hydroxyethylene dipeptide isostere and γ-amino acid derivative

An enantioselective synthesis of lactone 1, a precursor to the (2R,4S,5S) hydroxyethylene dipeptide isostere and amino acid AHPPA 2 has been accomplished from the common intermediate 5 employing Sharpless asymmetric aminohydroxylation as the key step.

Application of the lewis acid-lewis base bifunctional asymmetric catalysts to pharmaceutical syntheses: Stereoselective chiral building block syntheses of human immunodeficiency virus (HIV) protease inhibitor and β3- adenergic receptor agonist

Chiral building block syntheses of promising drugs were achieved using two types of catalytic stereoselective cyanosilylations of aldehydes promoted by Lewis acid-Lewis base bifunctional catalysts 1 and 2 as the key steps (diastereoselective cyanosilylation of amino aldehyde and enantioselective cyanosilylation). In the first part of this article, syntheses of chiral building blocks (6) of Atazanavir (3: human immunodeficiency virus (HIV) protease inhibitor) using the bifunctional catalyst 2 are discussed. The reaction of Boc-protected phenylalaninal 21 in the presence of 1 mol% catalyst 2 selectively afforded the anti isomer 22 as the major product (diastereomeric ratio=97:3), which was successively converted to the corresponding epoxide 6 in six steps. In the second part, we describe a chiral building block synthesis of β3-adrenergic receptor agonists. The enantioselective cyanosilylation of 3-chlorobenzaldehyde (38) with 9 mol% catalyst 1 gave the chiral cyanohydrin 39, which was converted to β-hydroxyethylamine 40 by reduction. Moreover, the chiral ligand of catalyst 1 could be recovered without column chromatography and reused without decreasing its activity.

Sulfinyl moiety as an internal nucleophile. Part 6: Stereospecific synthesis of 3-amino-2-hydroxy-4-phenylbutanoate

A novel and stereospecific synthesis of (2R,3S)-3-amino-2-hydroxy-4-phenylbutanoate (AHPBA) is disclosed. The key step includes regio- and stereospecific functionalization of an alkene by the pendant sulfinyl group.

Catalytic asymmetric direct α-amination reactions of 2-keto esters: A simple synthetic approach to optically active syn-β-amino-α-hydroxy esters

The catalytic enantioselective direct α-amination reaction of 2-keto esters with easily available azo dicarboxylates as the nitrogen source and chiral bisoxazoline-copper(II) complexes as the catalyst is presented. The reations proceed with excellent enan

Process for reducing α-amino ketones

The present invention has its objects to provide a method for reducing α-aminoketone derivatives under mild conditions with high stereoselectivity. This invention is a method for reducing α-aminoketone which comprises reacting an a-aminoketone derivative of general formula (1) with a compound prepared from an organoaluminum compound of general formula (4), a sulfonic acid derivative of general formula (5), and an alcohol compound of general formula (6) to give an α-aminoalcohol derivative of general formula (7)

New approaches to the asymmetric synthesis of dipeptide isosteres via β-Lactam Synthon Method

New and efficient synthetic routes to dipeptide isosteres with high enantiomeric purity, e.g., hydroxyethylene, dihydroxyethylene and hydroxyethylamine isosteres, have been developed via oxiranes 6 and formyloxazolines 13 derived from N-t-Boc-β-lactams 4.

Development of selective tight-binding inhibitors of leukotriene A4 hydrolase

Leukotriene A4 hydrolase is a zinc-containing enzyme which exhibits both epoxide hydrolase and aminopeptidase activities. Since the enzyme product leukotriene B4 is an inflammatory mediator, it is of interest to develop selective inh