62023-62-5

Usage

Chemical Properties

White solid

Upstream product

• 75523-28-3 5-benzyl-1,2-dihydropyrazol-3-one 
• 63158-17-8 methyl (E)-4-phenyl-2-butenoate 
• 73845-38-2 methyl 4-phenylbut-2-ynoate 
• 204587-95-1 (2S,3S)-tert-butyl 3-amino-2-hydroxy-4-phenylbutanoate 
• 54966-42-6 ethyl 3-benzylacrylate 
• 153291-28-2 (2S,3S)-3-(N,N-dibenzylamino)-2-hydroxy-4-phenylbutyric acid 
• 62023-59-0 (2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 
• 136354-01-3 N-methoxycarbonyl-1-methoxy-2-phenylethylamine 
• 75443-87-7 methyl DL-erythro-3-amino-2-hydroxy-4-phenylbutanoate 
• 6540-96-1 2-benzyl-4-pentenoic acid 
• 501-52-0 3-Phenylpropionic acid 
• 34541-75-8 methyl (Z)-4-phenyl-2-butenoate 
• 75414-66-3 methyl threo-3-hydroxy-2-tosyloxy-4-phenylbutanoate 
• 75414-69-6 methyl threo-2,3-dihydroxy-4-phenylbutanoate 

Downstream Products

• 62023-59-0 (2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 
• 176751-63-6 (2S,3S)-3-(ethoxycarbonyl)amino-2-hydroxy-4-phenylbutyric acid 
• 478411-22-2 (2S,3S)-3-(3-Acetoxy-2-methyl-benzoylamino)-2-hydroxy-4-phenyl-butyric acid 
• 749905-01-9 (2S,3S)-2-Acetoxy-3-(3-acetoxy-2-methyl-benzoylamino)-4-phenyl-butyric acid 
• 1303947-82-1 KNI-10859 
• 1303947-75-2 KNI-10857 
• 1303947-72-9 KNI-10838 
• 1303947-68-3 KNI-10856 
• 1303947-64-9 KNI-10605 

Relevant academic research and scientific papers

A case study of the MAC (masked acyl cyanide) oxyhomologation of N, N -dibenzyl-l-phenylalaninal with anti diastereoselectivity: Preparation of (2 S,3 S)-allophenylnorstatin esters

The three-component reaction between a protected α-amino aldehyde, an alcohol and an α-silyloxymalononitrile provides an expedient access to protected α-hydroxy-β-amino acid derivatives. The prototypical process, performed on N-Cbz-phenylalaninal, is known to proceed with syn diastereoselectivity. The present study demonstrates that the diastereoselectivity of the reaction can be inverted, using the rationale of a Felkin-Anh interaction model. Reactions performed on N,N-dibenzyl-l-phenylalaninal proceed with a high anti diastereoselectivity, providing a panel of synthetically useful ester derivatives of (2S,3S)-allophenylnorstatin. The procedure is exploited to accomplish one of the most efficient syntheses of the title compound to date, in 3 steps (66% yield) from N,N-dibenzyl-l-phenylalaninal.

Synthesis method of alpha-hydroxyl-beta-amino acid simplex stereoscopic isomer

The invention relates to a synthesis method of an alpha-hydroxyl-beta-amino acid simplex stereoscopic isomer. The method mainly solves the technical problems that an existing synthesis method uses expensive chiral ligand or highly-toxic raw materials and is not suitable for industrial production. The method includes the steps of firstly, synthesizing substitutive alpha-hydroxyl-beta-amino acid despinner according to a literature method; secondly, stereoscopically and selectively synthesizing an alpha-hydroxyl-beta-amino acid simplex isomer of an (S,S) structure and an alpha-hydroxyl-beta-aminoacid simplex isomer of an (R,R) structure with penicillin G acylase. The method is suitable for preparing the alpha-hydroxyl-beta-amino acid simplex isomers efficiently at low cost.

N -Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/br?nsted acid Co-catalyzed allylic C-H oxidation

A Pd(II)/bis-sulfoxide/Br?nsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and π-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.

Remarkable diastereomeric rearrangement of an α-acyloxy β-ketosulfide to an α-acyloxy thioester: A novel approach to the synthesis of optically active (2S,3S) β-amino α-hydroxy acids

A novel and efficient synthetic method is described for (2S,3S)-3-amino-2-hydroxy-4-phenyl butyric acid derivatives, which are useful intermediates of enzyme inhibitors. This involves a Pummerer rearrangement of a β-ketosulfoxide derived from L-phenylalanine followed by highly stereoselective acyl migration. From these studies, it appears that nitrogen-protecting groups exert a substantial influence over stereoselectivity. The mechanism of the rearrangement is discussed. β-Amino α-hydroxy carboxylic acids are important pharmaceutical intermediates, and this method may provide a versatile synthesis from various amino acids in a few steps.

PROCESSES FOR PRODUCING OXAZOLIDINONE DERIVATIVE OF BETA-HYDROXYETHYLAMINE COMPOUND AND FOR PRODUCING BETA-HYDROXYETHYLAMINE COMPOUND

The present invention provides a process of starting from N-alkoxycarbonyl-ethylamine compounds having a leaving group at the β-position to prepare oxazolidinone derivatives of β-hydroxyethylamine compounds having an inverted steric configuration at the β

First one-pot copper-catalyzed synthesis of α-hydroxy-β-amino acids in water. A new protocol for preparation of optically active norstatines

α-Hydroxy-β-amino acids were synthesized with excellent yields for the first time in water and by a simple procedure based on a copper catalytic cycle, which included the recovery and reuse of the catalyst and is possible to realize by using only water as reaction medium.

Chirospecific synthesis of the (2S,3R)- and (2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acids from sugar: Application to (-)-bestatin

The enantiomerically pure (2S,3R)- and (2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acids (AHPBA) were first obtained from sugar in a chirospecific manner. Additionally, the obtained (2S,3R)-AHPBA 1 was easily applied to the synthesis of (-)-bestatin.

Stereoselective cyanation of chiral α-amino aldehydes by reaction with Nagata's reagent: A route to enantiopure β-amino-α-hydroxy acids

Chiral α-dibenzylamino aldehydes react with diethylaluminum cyanide leading to anti-β-dibenzylamino-α-hydroxycyanides as the major diastereoisomers in good yields and diastereomeric excesses. Hydrolysis of the nitrile derivatives allows the synthesis of enantiopure β-amino-α-hydroxy acids.

A novel synthesis of allophenylnorstatine from (R)-aspartic acid

Highly stereoselective hydroxylation of all oxazoline-4-acetate 4 derived from (R)-aspartic acid followed by deprotection leads to allophenylnorstatine 1 in good yield.

Asymmetric synthesis of 3-amino-2-hydroxy-4-phenylbutanoate

Asymmetric synthesis of 3-amino-2-hydroxy-4-phenylbutanoate, a key component of the natural product bestatin and HIV protease inhibitors of KNI- 272 and R-87366, has been achieved from the stereoselective aldimine coupling reaction between 3-phenyl-2-aminopropanenitrile and (Z)-α-methoxy trimethylsilyl ketene acetal in the presence of Lewis acids.