128223-55-2

Usage

Chemical Properties

White powder

InChI:InChI=1/C10H13NO3.ClH/c11-8(9(12)10(13)14)6-7-4-2-1-3-5-7;/h1-5,8-9,12H,6,11H2,(H,13,14);1H/t8-,9+;/m1./s1

Upstream product

• 130115-05-8 (2S,3R)-3-Amino-2-hydroxy-4-phenyl-butyric acid isopropyl ester 
• 129867-99-8 (3-R)-2-acetoxy-3-isopropoxycarbonylamino-4-phenylbutyronitrile 
• 145872-15-7 (4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carboxylic acid ethyl ester 
• 673-06-3 D-(R)-phenylalanine 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 
• 129867-98-7 (R)-N-(isopropoxycarbonyl)phenylalaninal 
• 128223-47-2 (R)-N-(isopropoxycarbonyl)phenylalaninol 
• 128223-46-1 methyl (R)-N-(isopropoxycarbonyl)phenylalaninate 
• 21210-43-5 (S)-Methyl mandelate 
• 133187-22-1 (2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde 
• 133187-21-0 Methyl (S)-(+)-α-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α-phenylacetate 
• 139580-07-7 [Bis-(4-methoxy-phenyl)-methyl]-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-eth-(E)-ylidene]-amine 
• 130115-12-7 (S)-Benzyloxy-((4R,5S)-2-oxo-5-phenyl-oxazolidin-4-yl)-acetic acid isopropyl ester 
• 130115-09-2 (3S,4S)-3-Benzyloxy-1-[bis-(4-methoxy-phenyl)-methyl]-4-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-azetidin-2-one 

Downstream Products

• 1356606-78-4 (R)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-hydroxy-4-phenylbutanoic acid 
• 140409-03-6 methyl (2R,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate 
• 140409-02-5 methyl (2S,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate 
• 1455093-39-6 (2S,3R)-methyl 3-(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)-2-hydroxy-4-phenylbutanoate 
• 1455088-49-9 (2S,3R)-methyl 3-(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)-2-hydroxy-4-phenylbutanoic acid 

Relevant academic research and scientific papers

Anti- and syn-selective cyanosilylation reactions promoted by a sugar-based bifunctional catalyst: Stereoselective syntheses of essential building blocks for HIV protease inhibitors and bestatin

Chiral bifunctional catalyst 6 promoted anti- and syn-selective cyanosilylation reactions from chiral amino aldehydes derived from phenylalanine in excellent yields. Thus, from dibenzyl protected amino aldehyde 9, syn isomer was obtained as the major prod

Synthesis of α-Ketoamide-Based Stereoselective Calpain-1 Inhibitors as Neuroprotective Agents

Calpain inhibitors have been proposed as drug candidates for neurodegenerative disorders, with ABT-957 entering clinical trials for Alzheimer's disease and mild cognitive impairment. The structure of ABT-957 was very recently disclosed, and trials were te

Preparation of α-hydroxy-β-Fmoc amino acids from N-Boc amino acids

A general method for the conversion of N-Boc amino acids into their homologated α-hydroxy-β-Fmoc amino acids is described. The protocol involved preparation of the amino aldehyde by reduction of the corresponding Weinreb amides, hydrocyanation, and hydrol

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.

A Practical Synthesis of threo-3-Amino-2-hydroxycarboxylic Acids

An expeditious synthesis of (2R,3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid (2) and (2S,3R)-3-amino-2-hydroxy-4-phenylbutyric acid (4), the key components of the renin inhibitor (1) and bestatin (3), respectively, have been accomplished by featuring hi

A Stereoselective Synthesis of the (2R,3S)- and (2S,3R)-3-Amino-2-hydroxybutyric Acid Derivatives, the Key Components of a Renin Inhibitor and Bestatin

The title synthesis was achieved by featuring the -cycloaddition reaction of benzyloxyketene with a chiral imine derived from methyl (R)- or (S)-mandelate, alcoholysis of the formed 3,4-cis disubstituted β-lactam under acidic conditions, and reductiv

A stereospecific synthesis of (-)-bestatin from L-malic acid

A highly diastereospecific route to (-)-Bestatin from L-Malic Acid has been developed. This approach features a stereocontrolled alkylation of diethyl (S)-malate and proceeds through an oxazolidone via a Curtius Rearrangement.